814:
393:
75:
705:
721:
875:
198:
597:
424:) and the release of ring strain drives the reaction. Ring-closing metathesis, conversely, usually involves the formation of a five- or six-membered ring, which is enthalpically favorable; although these reactions tend to also evolve ethylene, as previously discussed. RCM has been used to close larger macrocycles, in which case the reaction may be kinetically controlled by running the reaction at high dilutions. The same substrates that undergo RCM can undergo acyclic diene metathesis, with ADMET favored at high concentrations. The
1226:
523:
788:
374:
221:
644:
752:
1130:
1009:
1071:
989:
887:
863:
1214:
492:
977:
844:
1503:
McCauley JA, McIntyre CJ, Rudd MT, Nguyen KT, Romano JJ, Butcher JW, Gilbert KF, Bush KJ, Holloway MK, Swestock J, Wan BL, Carroll SS, DiMuzio JM, Graham DJ, Ludmerer SW, Mao SS, Stahlhut MW, Fandozzi CM, Trainor N, Olsen DB, Vacca JP, Liverton NJ (March 2010). "Discovery of vaniprevir (MK-7009), a
807:
got involved in metathesis in 1972 and also proposed a metallacycle intermediate but one with four carbon atoms in the ring. The group he worked in reacted 1,4-dilithiobutane with tungsten hexachloride in an attempt to directly produce a cyclomethylenemetallacycle producing an intermediate, which
366:. The Chauvin mechanism involves the cycloaddition of an alkene double bond to a transition metal alkylidene to form a metallacyclobutane intermediate. The metallacyclobutane produced can then cycloeliminate to give either the original species or a new alkene and alkylidene. Interaction with the
758:
The three principal products C9, C10 and C11 are found in a 1:2:1 regardless of conversion. The same ratio is found with the higher oligomers. Chauvin also explained how the carbene forms in the first place: by alpha-hydride elimination from a carbon metal single bond. For example,
1023:
carbene complex While
Schrock focussed his research on tungsten and molybdenum catalysts for olefin metathesis, Grubbs started the development of catalysts based on ruthenium, which proved to be less sensitive to oxygen and water and therefore more
2593:
Wengrovius, Jeffrey H.; Schrock, Richard R.; Churchill, Melvyn Rowen; Missert, Joseph R.; Youngs, Wiley J. (1980). "Multiple metal-carbon bonds. 16. Tungsten-oxo alkylidene complexes as olefins metathesis catalysts and the crystal structure of
245:. This process interconverts propylene with ethylene and 2-butenes. Rhenium and molybdenum catalysts are used. Nowadays, only the reverse reaction, i.e., the conversion of ethylene and 2-butene to propylene is industrially practiced, however.
1616:
1669:
Sambasivarao Kotha; Kuldeep Singh (2007). "Cross-enyne and ring-closing metathesis cascade: A building-block approach suitable for diversity-oriented synthesis of densely functionalized macroheterocycles with amino acid scaffolds".
416:, can be favored but requires high pressures of ethylene to increase ethylene concentration in solution. The reverse reaction of RCM, ring-opening metathesis, can likewise be favored by a large excess of an alpha-olefin, often
1036:
In the 1960s and 1970s various groups reported the ring-opening polymerization of norbornene catalyzed by hydrated trichlorides of ruthenium and other late transition metals in polar, protic solvents. This prompted
2633:
Schrock, Richard R.; Murdzek, John S.; Bazan, Gui C.; Robbins, Jennifer; Dimare, Marcello; O'Regan, Marie (1990). "Synthesis of molybdenum imido alkylidene complexes and some reactions involving acyclic olefins".
2661:
Bazan, Guillermo C.; Oskam, John H.; Cho, Hyun Nam; Park, Lee Y.; Schrock, Richard R. (1991). "Living Ring-Opening
Metathesis Polymerization of 2,3-Difunctionalized 7-Oxanorbornenes and 7-Oxanorbornadienes by
2044:
Casey, Charles P.; Burkhardt, Terry J. (1974). "Reactions of (diphenylcarbene)pentacarbonyltungsten(0) with alkenes. Role of metal-carbene complexes in cyclopropanation and olefin metathesis reactions".
1882:
Jean-Louis Hérisson, Par; Chauvin, Yves (1971). "Catalyse de transformation des oléfines par les complexes du tungstène. II. Télomérisation des oléfines cycliques en présence d'oléfines acycliques".
1642:
Jean-Louis Hérisson, Par; Chauvin, Yves (1971). "Catalyse de transformation des oléfines par les complexes du tungstène. II. Télomérisation des oléfines cycliques en présence d'oléfines acycliques".
2539:
McLain, S. J.; Wood, C. D.; Schrock, R. R. (1979). "Preparation and characterization of tantalum(III) olefin complexes and tantalum(V) metallacyclopentane complexes made from acyclic α olefins".
1620:
715:
intermediate to explain the statistical distribution of products found in certain metathesis reactions. This mechanism is today considered the actual mechanism taking place in olefin metathesis.
2566:
Schrock, R; Rocklage, Scott; Wengrovius, Jeffrey; Rupprecht, Gregory; Fellmann, Jere (1980). "Preparation and characterization of active niobium, tantalum and tungsten metathesis catalysts".
1049:
as well as tungsten alkylidenes. They identified a Ru(II) carbene as an effective metal center and in 1992 published the first well-defined, ruthenium-based olefin metathesis catalyst, (PPh
4873:
307:
Molecular catalysts have been explored for the preparation of a variety of potential applications. the manufacturing of high-strength materials, the preparation of cancer-targeting
2766:
McConville, David H.; Wolf, Jennifer R.; Schrock, Richard R. (1993). "Synthesis of chiral molybdenum ROMP initiators and all-cis highly tactic poly(2,3-(R)2norbornadiene) (R = CF
1041:
and coworkers to search for well-defined, functional group tolerant catalysts based on ruthenium. The Grubbs group successfully polymerized the 7-oxo norbornene derivative using
954:
447:"Olefin metathesis is a child of industry and, as with many catalytic processes, it was discovered by accident." As part of ongoing work in what would later become known as
7088:
2331:
Porri, Lido; Rossi, Renzo; Diversi, Pietro; Lucherini, Antonio (1974). "Ring-Opening
Polymerization of Cycloolefins with Catalysts Derived from Ruthenium and Iridium".
3827:
956:
at low conversion was found to be consistent with the carbene mechanism. On the other hand, Grubbs did not rule out the possibility of a tetramethylene intermediate.
182:
compounds have mainly been investigated for small-scale reactions or in academic research. The homogeneous catalysts are often classified as
Schrock catalysts and
2419:
Nguyen, Sonbinh T.; Grubbs, Robert H.; Ziller, Joseph W. (1993). "Syntheses and activities of new single-component, ruthenium-based olefin metathesis catalysts".
2358:
Novak, Bruce M.; Grubbs, Robert H. (1988). "The ring opening metathesis polymerization of 7-oxabicyclohept-5-ene derivatives: a new acyclic polymeric ionophore".
2446:
Schwab, Peter; France, Marcia B.; Ziller, Joseph W.; Grubbs, Robert H. (1995). "A Series of Well-Defined
Metathesis Catalysts–Synthesis of and Its Reactions".
607:
first formulated two years earlier. Cyclobutanes have also never been identified in metathesis reactions, which is another reason why it was quickly abandoned.
358:
Hérisson and
Chauvin first proposed the widely accepted mechanism of transition metal alkene metathesis. The direct cycloaddition of two alkenes is formally
2269:
Michelotti, Francis W.; Keaveney, William P. (1965). "Coordinated
Polymerization of the Bicyclo-(2.2.1)-heptene-2 Ring System (Norbornene) in Polar Media".
813:
1178:
205:
Grubbs catalysts, on the other hand, are ruthenium(II) carbenoid complexes. Many variations of Grubbs catalysts are known. Some have been modified with a
1411:"Recent developments in design and synthesis of well-defined ruthenium metathesis catalysts – a highly successful opening for intricate organic synthesis"
2234:
Schrock, R. R.; Feldman, J.; Cannizzo, L. F.; Grubbs, R. H. (1987). "Ring-opening polymerization of norbornene by a living tungsten alkylidene complex".
1855:
Calderon, Nissim.; Ofstead, Eilert A.; Ward, John P.; Judy, W. Allen.; Scott, Kenneth W. (1968). "Olefin metathesis. I. Acyclic vinylenic hydrocarbons".
662:. No double bond migrations are observed; the reaction can be started with the butene and hexene as well and the reaction can be stopped by addition of
1828:
Calderon, N; Chen, Hung Yu; Scott, Kenneth W. (1967). "Olefin metathesis – A novel reaction for skeletal transformations of unsaturated hydrocarbons".
6204:
6149:
2099:
Grubbs, Robert H.; Carr, D. D.; Hoppin, C.; Burk, P. L. (1976). "Consideration of the mechanism of the metal catalyzed olefin metathesis reaction".
6917:
2207:
Gilliom, Laura R.; Grubbs, Robert H. (1986). "Titanacyclobutanes derived from strained, cyclic olefins: the living polymerization of norbornene".
6259:
638:. The researchers proposed a name for this reaction type: olefin metathesis. Formerly the reaction had been called "olefin disproportionation."
6409:
5043:
854:
this compound, a secondary reaction product of C12 with C6, would form well after formation of the two primary reaction products C12 and C16.
7232:
7138:
2296:
Rinehart, Robert E.; Smith, Homer P. (1965). "The
Emulsion Polymerization of the Norbornene Ring System Catalyzed by Noble Metal Compounds".
1410:
392:
983:
The Grubbs group then isolated the proposed metallacyclobutane intermediate in 1980 also with this reagent together with 3-methyl-1-butene:
61:
6912:
4738:
1539:
Kotha, S; Waghule GT (June 2012). "Diversity
Oriented Approach to Crownophanes by Enyne Metathesis and Diels–Alder Reaction as Key Steps".
6014:
3935:
6584:
5784:
4528:
1990:
Biefeld, Carol G.; Eick, Harry A.; Grubbs, Robert H. (1973). "Crystal structure of bis(triphenylphosphine)tetramethyleneplatinum(II)".
659:
114:
than alternative organic reactions. For their elucidation of the reaction mechanism and their discovery of a variety of highly active
6749:
6679:
6659:
6154:
5321:
4783:
3617:
5202:
4758:
3660:
3428:
830:
In 1975 Katz also arrived at a metallacyclobutane intermediate consistent with the one proposed by
Chauvin He reacted a mixture of
808:
yielded products identical with those produced by the intermediate in the olefin metathesis reaction. This mechanism is pairwise:
3971:
838:
catalyst and observed that the unsymmetrical C14 hydrocarbon reaction product is present right from the start at low conversion.
6504:
6982:
6932:
5336:
2890:(1990). "Living ring-opening metathesis polymerization catalyzed by well-characterized transition-metal alkylidene complexes".
1240:
530:
335:
237:
using catalysts developed well before the Nobel-Prize winning work on homogeneous complexes. Representative processes include:
6439:
2153:
Howard, T. R.; Lee, J. B.; Grubbs, R. H. (1980). "Titanium metallacarbene-metallacyclobutane reactions: stepwise metathesis".
381:
Olefin metathesis involves little change in enthalpy for unstrained alkenes. Product distributions are determined instead by
197:
7078:
6887:
6544:
6524:
6484:
5291:
4234:
1313:
704:
1963:
Grubbs, Robert H.; Brunck, Terence K. (1972). "Possible intermediate in the tungsten-catalyzed olefin metathesis reaction".
774:
a few years earlier independently came up with a competing mechanism. It consisted of a tetramethylene intermediate with sp
720:
7073:
7003:
6902:
6559:
6414:
6044:
5889:
5499:
5126:
4903:
1909:
S. Lewandos, G; Pettit, R. (1971). "A proposed mechanism for the metal-catalysed disproportionation reaction of olefins".
7153:
6937:
6249:
5739:
5414:
3675:
2951:
Samojłowicz, C.; Grela, K. (2009). "Ruthenium-Based Olefin Metathesis Catalysts Bearing N-Heterocyclic Carbene Ligands".
1732:
Truett, W. L.; Johnson, D. R.; Robinson, I. M.; Montague, B. A. (1960). "Polynorbornene by Coördination Polymerization".
881:
with a 5-membered cycle in another round of isotope labeling studies in favor of the 4-membered cycle Chauvin mechanism:
5959:
2914:; Hoveyda, A. H. (2003). "Molybdenum and Tungsten Imido Alkylidene Complexes as Efficient Olefin-Metathesis Catalysts".
370:
on the metal catalyst lowers the activation energy enough that the reaction can proceed rapidly at modest temperatures.
7148:
6862:
6724:
6514:
6479:
3767:
820:
In 1973 Grubbs found further evidence for this mechanism by isolating one such metallacycle not with tungsten but with
275:
and 1,9-decadiene, useful crosslinking agents and synthetic intermediates, are produced commercially by ethenolysis of
517:
breaking a CC bond and forming a new alkylidene-titanium bond; the process then repeats itself with a second monomer:
7237:
7038:
6977:
6509:
6424:
6394:
6374:
6239:
6234:
5609:
5534:
5177:
5131:
4998:
4259:
3413:
3174:
1617:"Dow Corning and Elevance Announce Partnership to Market Naturally Derived Ingredients in Personal Care Applications"
1487:
596:
1164:, metathesis was established with cis-2-pentene. In another development, certain tungsten oxo complexes of the type
959:
The first practical metathesis system was introduced in 1978 by Tebbe based on the (what later became known as the)
874:
7143:
7103:
7053:
6729:
6529:
6279:
6209:
4698:
4269:
3802:
3797:
3762:
615:
6344:
5237:
4958:
3458:
214:
6897:
6739:
6609:
6604:
6419:
5894:
5804:
5394:
5326:
5217:
4793:
4548:
4473:
3928:
3812:
3807:
3792:
2180:
Stille, John R.; Grubbs, Robert H. (1986). "Synthesis of (.+-.)-.DELTA.9,12-capnellene using titanium reagents".
1225:
373:
6654:
787:
522:
7242:
7183:
7068:
6967:
6907:
6554:
6349:
6309:
6284:
6194:
5654:
4688:
4618:
4254:
4184:
3817:
3695:
1443:
Ghashghaee, Mohammad (2018). "Heterogeneous catalysts for gas-phase conversion of ethylene to higher olefins".
1015:
In that same year the Grubbs group proved that metathesis polymerization of norbornene by Tebbe's reagent is a
779:
191:
5774:
1697:
Ziegler, Karl; Holzkamp, E.; Breil, H.; Martin, H. (1955). "Polymerisation von Äthylen und anderen Olefinen".
408:, which can be removed from the system because they are gases. Because of this CM and RCM reactions often use
7247:
7173:
6759:
6649:
6269:
5994:
5779:
5724:
5569:
5529:
5361:
5116:
4833:
4683:
3610:
2387:"Ring-opening metathesis polymerization (ROMP) of norbornene by a Group VIII carbene complex in protic media"
2126:
Tebbe, F. N.; Parshall, G. W.; Reddy, G. S. (1978). "Olefin homologation with titanium methylene compounds".
739:
7133:
6694:
6139:
220:
7168:
7083:
7058:
7033:
7018:
6942:
6857:
6754:
6714:
6579:
6534:
6299:
5844:
5829:
5694:
5484:
5152:
4908:
4588:
4563:
4533:
4124:
3388:
1019:
system and a year later Grubbs and Schrock co-published an article describing living polymerization with a
242:
2072:
Grubbs, Robert H.; Burk, Patrick L.; Carr, Dale D. (1975). "Mechanism of the olefin metathesis reaction".
794:
Experimental support offered by Pettit for this mechanism was based on an observed reaction inhibition by
643:
46:
7118:
7063:
7008:
6719:
6639:
6539:
6254:
6219:
6064:
5954:
5669:
5664:
5489:
5449:
5346:
5157:
5121:
4973:
4963:
4818:
4678:
4538:
4488:
4483:
4458:
4418:
4364:
4129:
4119:
4094:
3868:
3393:
1936:
Lewandos, Glenn S.; Pettit, R. (1971). "Mechanism of the metal-catalyzed disproportionation of olefins".
1364:
900:
611:
604:
499:
448:
382:
359:
248:
1129:
751:
7093:
6794:
6599:
6034:
5919:
5599:
5574:
5514:
5371:
5106:
4813:
4593:
4558:
4463:
4154:
4089:
3921:
3873:
549:
54:
6384:
4648:
3025:(2001). "The Development of L2X2Ru=CHR Olefin Metathesis Catalysts: An Organometallic Success Story".
1213:
1070:
1008:
988:
886:
7193:
7098:
6952:
6832:
6804:
6774:
6689:
6619:
6574:
6549:
6469:
6369:
6329:
6024:
5644:
5634:
5559:
5083:
4943:
4938:
4918:
4603:
4400:
4379:
4339:
4264:
3685:
3584:
3065:; Chang, S. (1998). "Recent advances in olefin metathesis and its application in organic synthesis".
2386:
4084:
2879:
2838:
2752:
1774:
Natta, G.; Dall'asta, G.; Mazzanti, G. (1964). "Stereospecific Homopolymerization of Cyclopentene".
1575:
1329:
Astruc D. (2005). "The metathesis reactions: from a historical perspective to recent developments".
7158:
7048:
7028:
6892:
6734:
6644:
6614:
6594:
6489:
6444:
6274:
6184:
6114:
5999:
5989:
5819:
5376:
5316:
5281:
5088:
5068:
5028:
4803:
4673:
4638:
4598:
4349:
4189:
4179:
4109:
3757:
3721:
3626:
3603:
3564:
1576:"Synthesis of Fluorine-18 Functionalized Nanoparticles for use as in vivo Molecular Imaging Agents"
1271:
1097:
was also shown to be active. This work culminated in the now commercially available 1st generation
976:
425:
341:
131:
6624:
1418:
862:
491:
7128:
6987:
6837:
6779:
6704:
6684:
6404:
6354:
6214:
6179:
6119:
6049:
5604:
5351:
5331:
5063:
4983:
4878:
4838:
4808:
4743:
4628:
4613:
4523:
4513:
4174:
4099:
4054:
3524:
560:
400:
Cross metathesis and ring-closing metathesis are driven by the entropically favored evolution of
329:
233:
Olefin metathesis has several industrial applications. Almost all commercial applications employ
147:
4389:
255:) for conversion to detergents. The process recycles certain olefin fractions using metathesis.
6867:
6589:
6339:
6319:
6294:
6244:
6159:
6134:
6089:
6059:
6039:
6009:
5974:
5929:
5904:
5879:
5764:
5689:
5469:
5162:
5098:
4898:
4623:
4543:
4229:
4204:
3981:
3976:
3902:
3787:
3519:
3398:
2473:
Schwab, Peter; Grubbs, Robert H.; Ziller, Joseph W. (1996). "Synthesis and Applications of RuCl
1078:
483:
467:
367:
234:
843:
150:. The heterogeneous catalysts are often prepared by in-situ activation of a metal halide (MCl
7203:
6789:
6744:
6459:
6429:
6399:
6334:
6314:
6229:
6224:
6189:
6144:
6129:
6124:
6104:
6094:
6029:
6019:
5949:
5899:
5419:
5222:
4798:
4753:
4583:
4573:
4319:
4244:
4039:
4001:
3822:
3443:
3167:
2866:
2825:
2739:
1042:
1016:
851:
775:
764:
623:
564:
4249:
106:. Because of the relative simplicity of olefin metathesis, it often creates fewer undesired
6972:
6922:
6872:
6852:
6842:
6699:
6674:
6389:
6379:
6264:
6079:
6074:
6004:
5789:
5589:
5549:
5479:
5444:
5399:
5366:
5232:
5207:
5187:
5008:
4968:
4928:
4893:
4823:
4578:
4448:
4423:
3961:
3777:
3640:
3453:
3433:
3370:
2846:
2305:
2243:
1706:
968:
736:
651:
534:
311:, and the conversion of renewable plant-based feedstocks into hair and skin care products.
74:
2805:
1801:
Banks, R. L.; Bailey, G. C. (1964). "Olefin Disproportionation. A New Catalytic Process".
1382:
R.R. Schrock (1986). "High-oxidation-state molybdenum and tungsten alkylidene complexes".
857:
In 1974 Casey was the first to implement carbenes into the metathesis reaction mechanism:
261:
production, which involves ethenolysis of isobutene dimers. The catalyst is derived from
8:
7178:
7163:
6809:
6784:
6769:
6764:
6494:
6449:
6434:
6324:
6304:
6199:
6084:
6069:
5914:
5859:
5849:
5814:
5579:
5454:
5429:
5341:
5197:
5182:
5167:
4988:
4933:
4703:
4553:
4498:
4369:
4284:
4144:
4069:
3897:
3716:
3690:
3645:
3423:
3403:
3374:
3361:
688:
with deuterium evenly distributed. In this way they were able to differentiate between a
295:
7188:
5839:
5023:
4214:
2984:(2010). "Ruthenium-Based Heterocyclic Carbene-Coordinated Olefin Metathesis Catalysts".
2309:
2247:
2017:
Katz, Thomas J.; McGinnis, James (1975). "Mechanism of the olefin metathesis reaction".
1710:
186:. Schrock catalysts feature molybdenum(VI)- and tungsten(VI)-based centers supported by
6927:
6877:
6847:
6709:
6499:
6289:
6174:
6109:
6099:
5864:
5794:
5759:
5754:
5734:
5729:
5674:
5584:
5434:
5296:
5286:
5192:
4978:
4923:
4853:
4773:
4668:
4568:
4503:
4428:
4274:
4139:
4074:
4059:
3711:
3665:
3514:
3488:
3418:
3136:
3111:
3050:
3009:
2939:
2911:
2887:
1460:
1346:
1046:
584:
553:
503:
276:
159:
127:
3078:
1922:
1841:
6664:
5984:
5869:
5834:
5799:
5744:
5699:
5614:
5594:
5544:
5539:
5509:
5494:
5404:
5311:
5247:
5212:
5038:
4788:
4713:
4693:
4608:
4443:
4438:
4384:
4294:
4199:
4159:
4114:
3996:
3991:
3956:
3892:
3853:
3782:
3554:
3468:
3438:
3379:
3141:
3042:
3001:
2968:
2931:
2579:
1598:
1556:
1521:
1483:
1464:
1309:
1261:
1256:
363:
262:
83:
5659:
3054:
2943:
2512:
Schrock, R. R.; Meakin, P. (1974). "Pentamethyl complexes of niobium and tantalum".
2385:
Nguyen, Sonbinh T.; Johnson, Lynda K.; Grubbs, Robert H.; Ziller, Joseph W. (1992).
1350:
1305:
435:
of an alkene to two ketone fragments followed by the reaction of one of them with a
7198:
7043:
7013:
6957:
6882:
6814:
6569:
6519:
6364:
6169:
5944:
5939:
5884:
5874:
5649:
5459:
5439:
5409:
5306:
5242:
5227:
5058:
5013:
5003:
4993:
4888:
4868:
4863:
4848:
4843:
4723:
4718:
4658:
4643:
4633:
4478:
4468:
4334:
4324:
4224:
4219:
4194:
4134:
3986:
3945:
3858:
3752:
3655:
3650:
3534:
3463:
3448:
3160:
3131:
3123:
3098:
3086:
3074:
3062:
3034:
3022:
3013:
2993:
2981:
2960:
2923:
2899:
2854:
2813:
2783:
2727:
2643:
2615:
2575:
2548:
2521:
2494:
2455:
2428:
2401:
2367:
2340:
2313:
2278:
2251:
2216:
2189:
2162:
2135:
2108:
2081:
2054:
2026:
1999:
1972:
1945:
1918:
1891:
1864:
1837:
1810:
1783:
1741:
1714:
1679:
1651:
1590:
1548:
1513:
1452:
1391:
1338:
1301:
1266:
1157:
1038:
1025:
804:
669:
The Goodyear group demonstrated that the reaction of regular 2-butene with its all-
568:
171:
123:
91:
4314:
431:
Cross-metathesis is synthetically equivalent to (and has replaced) a procedure of
178:. Commercial catalysts are often based on molybdenum and ruthenium. Well-defined
7108:
6799:
6634:
6629:
5924:
5909:
5854:
5809:
5769:
5719:
5684:
5679:
5624:
5619:
5554:
5504:
5424:
5252:
5136:
5111:
5073:
5048:
5033:
5018:
4953:
4828:
4778:
4768:
4748:
4708:
4518:
4508:
4493:
4289:
4209:
4079:
4049:
4034:
4029:
3731:
3726:
3574:
3544:
3473:
1161:
1098:
996:
795:
694:
183:
155:
111:
2344:
1895:
1655:
541:
in 1964 also observed the formation of an unsaturated polymer when polymerizing
7113:
7023:
6962:
6054:
5964:
5934:
5709:
5564:
5301:
5078:
4948:
4763:
4733:
4433:
4329:
4104:
3966:
3848:
3747:
3670:
3569:
3559:
2317:
2282:
1368:
1109:
Schrock entered the olefin metathesis field in 1979 as an extension of work on
799:
771:
631:
475:
436:
179:
3913:
3112:"Progress in metathesis chemistry (Editorial for Open Access Thematic Series)"
3102:
2858:
2817:
1760:
1619:(Press release). Elevance Renewable Sciences. 9 September 2008. Archived from
428:
may also be exploited to improve both reaction rates and product selectivity.
7226:
7123:
6824:
6669:
6564:
6359:
5749:
5714:
5704:
5639:
5629:
5519:
5356:
5172:
4883:
4858:
4728:
4374:
4359:
4344:
4239:
4169:
4149:
4064:
3843:
3529:
3504:
3408:
1718:
1237:
960:
869:
Grubbs in 1976 provided evidence against his own updated pairwise mechanism:
743:
460:
409:
272:
252:
99:
1456:
16:
Organic reaction involving the breakup and reassembly of alkene double bonds
6164:
5524:
5276:
5053:
4653:
4453:
4304:
4299:
4164:
4019:
3595:
3579:
3509:
3483:
3145:
3046:
3005:
2972:
2935:
2927:
2459:
1787:
1683:
1602:
1560:
1525:
1408:
728:
712:
673:
542:
538:
514:
308:
119:
103:
4663:
4309:
4279:
4044:
3772:
3539:
831:
588:
413:
347:
280:
2903:
2787:
2731:
2647:
2619:
2552:
2525:
2432:
2405:
2371:
2255:
2220:
2193:
2166:
2139:
2112:
2085:
2058:
2030:
2003:
1976:
1949:
1868:
1814:
1745:
1395:
6947:
6474:
5824:
3549:
3365:
3127:
1803:
Industrial & Engineering Chemistry Product Research and Development
1153:
1000:
835:
670:
548:
In a third development leading up to olefin metathesis, researchers at
507:
506:
a RTiX titanium intermediate first coordinates to the double bond in a
471:
432:
421:
107:
3038:
2997:
2964:
2498:
1594:
1552:
1517:
420:. Ring-opening metathesis usually involves a strained alkene (often a
78:
Reaction scheme of the olefin metathesis – changing groups are colored
3884:
3680:
1342:
1244:
964:
760:
732:
619:
572:
511:
405:
258:
206:
143:
115:
529:
Only much later the polynorbornene was going to be produced through
4354:
4024:
3197:
1149:
1121:
1110:
1020:
894:
821:
663:
655:
580:
576:
557:
456:
452:
401:
187:
2565:
2485:: The Influence of the Alkylidene Moiety on Metathesis Activity".
1477:
4014:
3282:
3248:
3214:
2592:
1113:
alkylidenes. The initial result was disappointing as reaction of
627:
417:
386:
175:
3383:
3333:
3316:
3299:
3265:
3231:
3183:
1668:
650:
In this reaction 2-pentene forms a rapid (a matter of seconds)
266:
210:
95:
1731:
1295:
1233:
1124:
yielded only a metallacyclopentane, not metathesis products:
727:
Chauvin's experimental evidence was based on the reaction of
603:
This particular mechanism is symmetry forbidden based on the
486:(a patent by this company on this topic dates back to 1955),
2233:
798:
in certain metathesis reactions of 4-nonene with a tungsten
2979:
963:. In a model reaction isotopically labeled carbon atoms in
3828:
Arene complexes of univalent gallium, indium, and thallium
3152:
2632:
2330:
1881:
1773:
1696:
1641:
1504:
macrocyclic hepatitis C virus NS3/4a protease inhibitor".
1502:
778:
carbon atoms linked to a central metal atom with multiple
2384:
850:
In any of the pairwise mechanisms with olefin pairing as
2445:
1409:
Ileana Dragutan; Valerian Dragutan; Petru Filip (2005).
618:
described a novel catalyst system for the metathesis of
1854:
1296:
Lionel Delaude; Alfred F. Noels (2005). "Metathesis".
2910:
2765:
903:
591:(they called it a quasicyclobutane) – metal complex:
319:
Some important classes of olefin metathesis include:
7089:
Erlenmeyer–Plöchl azlactone and amino-acid synthesis
2950:
2098:
459:instead of a saturated long-chain hydrocarbon (see
412:. The reverse reaction of CM of two alpha-olefins,
3020:
2472:
2448:Angewandte Chemie International Edition in English
2418:
2298:Journal of Polymer Science Part B: Polymer Letters
2268:
2125:
1776:Angewandte Chemie International Edition in English
948:
6150:Divinylcyclopropane-cycloheptadiene rearrangement
2660:
2538:
2271:Journal of Polymer Science Part A: General Papers
1989:
1908:
1827:
302:
7224:
146:. Most commercially important processes employ
94:that entails the redistribution of fragments of
3943:
3061:
2152:
1538:
1298:Kirk-Othmer Encyclopedia of Chemical Technology
1220:The first asymmetric catalyst followed in 1993
826:cis-bis(triphenylphosphine)dichloroplatinum(II)
763:(C3) forms in a reaction of 2-butene (C4) with
6410:Thermal rearrangement of aromatic hydrocarbons
5044:Thermal rearrangement of aromatic hydrocarbons
2071:
2043:
1935:
7139:Lectka enantioselective beta-lactam synthesis
4399:
3929:
3611:
3168:
2511:
2295:
2206:
396:Classification of Olefin metathesis reactions
6918:Inverse electron-demand Diels–Alder reaction
4739:Heterogeneous metal catalyzed cross-coupling
3625:
2179:
2016:
1962:
1573:
1381:
571:supported on alumina for example converting
6260:Lobry de Bruyn–Van Ekenstein transformation
2357:
1800:
1478:Klaus Weissermel, Hans-Jurgen Arpe (1997).
3936:
3922:
3712:Oxidative addition / reductive elimination
3618:
3604:
3175:
3161:
1758:A. W. Anderson and N. G. Merckling, U. S.
1442:
498:a reaction then classified as a so-called
451:Karl Ziegler discovered the conversion of
6750:Petrenko-Kritschenko piperidone synthesis
6205:Fritsch–Buttenberg–Wiechell rearrangement
3135:
1471:
1328:
711:In 1971 Chauvin proposed a four-membered
6913:Intramolecular Diels–Alder cycloaddition
3661:Polyhedral skeletal electron pair theory
2776:Journal of the American Chemical Society
2636:Journal of the American Chemical Society
2608:Journal of the American Chemical Society
2541:Journal of the American Chemical Society
2514:Journal of the American Chemical Society
2487:Journal of the American Chemical Society
2421:Journal of the American Chemical Society
2394:Journal of the American Chemical Society
2360:Journal of the American Chemical Society
2209:Journal of the American Chemical Society
2182:Journal of the American Chemical Society
2155:Journal of the American Chemical Society
2128:Journal of the American Chemical Society
2101:Journal of the American Chemical Society
2074:Journal of the American Chemical Society
2047:Journal of the American Chemical Society
2019:Journal of the American Chemical Society
1965:Journal of the American Chemical Society
1938:Journal of the American Chemical Society
1857:Journal of the American Chemical Society
1734:Journal of the American Chemical Society
1583:Journal of the American Chemical Society
1232:With a Schrock catalyst modified with a
995:They isolated a similar compound in the
770:In the same year Pettit who synthesised
201:Commercially available schrock catalysts
73:
2916:Angewandte Chemie International Edition
2886:
1482:(3rd ed.). John Wiley & Sons.
824:by reaction of the dilithiobutane with
7225:
6933:Metal-centered cycloaddition reactions
6585:Debus–Radziszewski imidazole synthesis
4529:Bodroux–Chichibabin aldehyde synthesis
3116:Beilstein Journal of Organic Chemistry
3085:
2806:"Olefin Metathesis: Big-Deal Reaction"
1208:were commercialized starting in 1990.
545:with tungsten and molybdenum halides.
531:ring opening metathesis polymerisation
442:
336:Ring-opening metathesis polymerization
7079:Diazoalkane 1,3-dipolar cycloaddition
6983:Vinylcyclopropane (5+2) cycloaddition
6888:Diazoalkane 1,3-dipolar cycloaddition
6660:Hurd–Mori 1,2,3-thiadiazole synthesis
6155:Dowd–Beckwith ring-expansion reaction
5322:Hurd–Mori 1,2,3-thiadiazole synthesis
4398:
4235:LFER solvent coefficients (data page)
3917:
3599:
3156:
3109:
1672:European Journal of Organic Chemistry
1243:leading to highly stereoregular cis,
7233:Carbon-carbon bond forming reactions
5890:Sharpless asymmetric dihydroxylation
5127:Methoxymethylenetriphenylphosphorane
3768:Transition metal fullerene complexes
1438:
1436:
1291:
1289:
1287:
1136:But by tweaking this structure to a
1104:
32:Carbon-carbon bond forming reaction
6015:Allen–Millar–Trippett rearrangement
3110:Grela, K. (2010). Grela, K. (ed.).
2847:"Olefin Metathesis: The Early Days"
1365:"The Nobel Prize in Chemistry 2005"
1031:
949:{\displaystyle (d_{4},d_{2},d_{0})}
130:were collectively awarded the 2005
13:
7154:Nitrone-olefin (3+2) cycloaddition
7149:Niementowski quinazoline synthesis
6938:Nitrone-olefin (3+2) cycloaddition
6863:Azide-alkyne Huisgen cycloaddition
6725:Niementowski quinazoline synthesis
6480:Azide-alkyne Huisgen cycloaddition
5785:Meerwein–Ponndorf–Verley reduction
5337:Leimgruber–Batcho indole synthesis
3803:Transition metal carbyne complexes
3798:Transition metal carbene complexes
3763:Transition metal indenyl complexes
2798:
1181:for olefin metathesis of the type
391:
372:
283:. The catalyst is derived from Re
219:
196:
102:and regeneration of carbon-carbon
14:
7259:
6978:Trimethylenemethane cycloaddition
6680:Johnson–Corey–Chaykovsky reaction
6545:Cadogan–Sundberg indole synthesis
6525:Bohlmann–Rahtz pyridine synthesis
6485:Baeyer–Emmerling indole synthesis
5292:Cadogan–Sundberg indole synthesis
4784:Johnson–Corey–Chaykovsky reaction
3813:Transition metal alkyne complexes
3808:Transition metal alkene complexes
1433:
1284:
1175:were also found to be effective.
502:. According to the then proposed
7074:Cook–Heilbron thiazole synthesis
6903:Hexadehydro Diels–Alder reaction
6730:Niementowski quinoline synthesis
6560:Cook–Heilbron thiazole synthesis
6505:Bischler–Möhlau indole synthesis
6415:Tiffeneau–Demjanov rearrangement
6045:Baker–Venkataraman rearrangement
5203:Horner–Wadsworth–Emmons reaction
4874:Mizoroki-Heck vs. Reductive Heck
4759:Horner–Wadsworth–Emmons reaction
4270:Neighbouring group participation
3818:Transition-metal allyl complexes
3429:Horner–Wadsworth–Emmons reaction
1541:The Journal of Organic Chemistry
1224:
1212:
1128:
1069:
1007:
987:
975:
885:
873:
861:
842:
812:
786:
750:
719:
703:
642:
616:Goodyear Tire and Rubber Company
610:Then in 1967 researchers led by
595:
521:
490:
6610:Fiesselmann thiophene synthesis
6440:Westphalen–Lettré rearrangement
6420:Vinylcyclopropane rearrangement
6250:Kornblum–DeLaMare rearrangement
5895:Epoxidation of allylic alcohols
5805:Noyori asymmetric hydrogenation
5740:Kornblum–DeLaMare rearrangement
5415:Gallagher–Hollander degradation
3793:Transition metal acyl complexes
2759:
2654:
2626:
2586:
2559:
2532:
2505:
2466:
2439:
2412:
2378:
2351:
2324:
2289:
2262:
2227:
2200:
2173:
2146:
2119:
2092:
2065:
2037:
2010:
1983:
1956:
1929:
1902:
1875:
1848:
1821:
1794:
1767:
1752:
1725:
1690:
1662:
1635:
1609:
1567:
1445:Reviews in Chemical Engineering
1306:10.1002/0471238961.metanoel.a01
834:, 2-butene and 4-octene with a
780:three-center two-electron bonds
241:The Phillips Triolefin and the
228:
7069:Chichibabin pyridine synthesis
6555:Chichibabin pyridine synthesis
6515:Blum–Ittah aziridine synthesis
6350:Ring expansion and contraction
4619:Cross dehydrogenative coupling
2568:Journal of Molecular Catalysis
1532:
1506:Journal of Medicinal Chemistry
1496:
1402:
1375:
1357:
1322:
943:
904:
303:Homogeneous catalyst potential
1:
7039:Bischler–Napieralski reaction
6997:Heterocycle forming reactions
6650:Hemetsberger indole synthesis
6510:Bischler–Napieralski reaction
6425:Wagner–Meerwein rearrangement
6395:Sommelet–Hauser rearrangement
6375:Seyferth–Gilbert homologation
6240:Ireland–Claisen rearrangement
6235:Hofmann–Martius rearrangement
5995:2,3-sigmatropic rearrangement
5610:Corey–Winter olefin synthesis
5535:Barton–McCombie deoxygenation
5178:Corey–Winter olefin synthesis
5132:Seyferth–Gilbert homologation
4999:Seyferth–Gilbert homologation
3414:Corey–Winter olefin synthesis
3089:(2004). "Olefin metathesis".
3079:10.1016/S0040-4020(97)10427-6
3027:Accounts of Chemical Research
2892:Accounts of Chemical Research
1923:10.1016/S0040-4039(01)96558-X
1842:10.1016/S0040-4039(01)89881-6
1574:Matson JB, Grubbs RH (2008).
1384:Accounts of Chemical Research
1277:
740:tungsten(VI) oxytetrachloride
533:. The DuPont work was led by
326:Ring-opening metathesis (ROM)
7144:Lehmstedt–Tanasescu reaction
7104:Gabriel–Colman rearrangement
7059:Bucherer carbazole synthesis
7054:Borsche–Drechsel cyclization
7034:Bernthsen acridine synthesis
7019:Bamberger triazine synthesis
7004:Algar–Flynn–Oyamada reaction
6715:Nazarov cyclization reaction
6580:De Kimpe aziridine synthesis
6535:Bucherer carbazole synthesis
6530:Borsche–Drechsel cyclization
6300:Nazarov cyclization reaction
6280:Meyer–Schuster rearrangement
6210:Gabriel–Colman rearrangement
5960:Wolffenstein–Böters reaction
5845:Reduction of nitro compounds
5695:Grundmann aldehyde synthesis
5500:Algar–Flynn–Oyamada reaction
4909:Olefin conversion technology
4904:Nozaki–Hiyama–Kishi reaction
4699:Gabriel–Colman rearrangement
4589:Claisen-Schmidt condensation
4534:Bouveault aldehyde synthesis
2580:10.1016/0304-5102(80)87006-4
1480:Industrial Organic Chemistry
510:. The second step then is a
480:lithium aluminum tetraheptyl
353:
243:Olefin conversion technology
137:
7:
7119:Hantzsch pyridine synthesis
6898:Enone–alkene cycloadditions
6720:Nenitzescu indole synthesis
6640:Hantzsch pyridine synthesis
6605:Ferrario–Ackermann reaction
6255:Kowalski ester homologation
6220:Halogen dance rearrangement
6065:Benzilic acid rearrangement
5490:Akabori amino-acid reaction
5450:Von Braun amide degradation
5395:Barbier–Wieland degradation
5347:Nenitzescu indole synthesis
5327:Kharasch–Sosnovsky reaction
5218:Julia–Kocienski olefination
5122:Kowalski ester homologation
4819:Kowalski ester homologation
4794:Julia–Kocienski olefination
4549:Cadiot–Chodkiewicz coupling
4474:Aza-Baylis–Hillman reaction
4419:Acetoacetic ester synthesis
4130:Dynamic binding (chemistry)
4120:Conrotatory and disrotatory
4095:Charge remote fragmentation
3869:Shell higher olefin process
3676:Dewar–Chatt–Duncanson model
3182:
2345:10.1002/macp.1974.021751106
1896:10.1002/macp.1971.021410112
1656:10.1002/macp.1971.021410112
1250:
500:coordination polymerization
470:research group polymerized
377:Olefin metathesis mechanism
249:Shell higher olefin process
10:
7264:
7184:Robinson–Gabriel synthesis
7134:Kröhnke pyridine synthesis
6968:Retro-Diels–Alder reaction
6908:Imine Diels–Alder reaction
6695:Kröhnke pyridine synthesis
6310:Newman–Kwart rearrangement
6285:Mislow–Evans rearrangement
6195:Fischer–Hepp rearrangement
6140:Di-π-methane rearrangement
5920:Stephen aldehyde synthesis
5655:Eschweiler–Clarke reaction
5372:Williamson ether synthesis
4689:Fujiwara–Moritani reaction
4594:Combes quinoline synthesis
4559:Carbonyl olefin metathesis
4260:More O'Ferrall–Jencks plot
4185:Grunwald–Winstein equation
4155:Electron-withdrawing group
4090:Catalytic resonance theory
3758:Cyclopentadienyl complexes
3722:β-hydride elimination
3696:Metal–ligand multiple bond
2333:Die Makromolekulare Chemie
2318:10.1002/pol.1965.110031215
2283:10.1002/pol.1965.100030305
1884:Die Makromolekulare Chemie
1644:Die Makromolekulare Chemie
583:for which they proposed a
550:Phillips Petroleum Company
7194:Urech hydantoin synthesis
7174:Pomeranz–Fritsch reaction
7099:Fischer oxazole synthesis
6996:
6833:1,3-Dipolar cycloaddition
6823:
6805:Urech hydantoin synthesis
6775:Reissert indole synthesis
6760:Pomeranz–Fritsch reaction
6690:Knorr quinoline synthesis
6620:Fischer oxazole synthesis
6550:Camps quinoline synthesis
6470:1,3-Dipolar cycloaddition
6458:
6370:Semipinacol rearrangement
6345:Ramberg–Bäcklund reaction
6330:Piancatelli rearrangement
6270:McFadyen–Stevens reaction
6025:Alpha-ketol rearrangement
5973:
5780:McFadyen–Stevens reaction
5725:Kiliani–Fischer synthesis
5645:Elbs persulfate oxidation
5570:Bouveault–Blanc reduction
5530:Baeyer–Villiger oxidation
5468:
5385:
5362:Schotten–Baumann reaction
5265:
5238:Ramberg–Bäcklund reaction
5145:
5117:Kiliani–Fischer synthesis
5097:
4959:Ramberg–Bäcklund reaction
4944:Pinacol coupling reaction
4939:Piancatelli rearrangement
4834:Liebeskind–Srogl coupling
4684:Fujimoto–Belleau reaction
4407:
4401:List of organic reactions
4265:Negative hyperconjugation
4010:
3952:
3882:
3836:
3823:Transition metal carbides
3740:
3704:
3633:
3585:Friedel-Crafts Alkylation
3497:
3459:Ramberg–Bäcklund reaction
3354:
3190:
3103:10.1016/j.tet.2004.05.124
2859:10.1021/cen-v080n029.p034
2818:10.1021/cen-v080n016.p029
1417:: 105–129. Archived from
767:and tetramethyltin (C1).
552:in 1964 described olefin
68:
42:Organic Chemistry Portal
36:
23:
7238:Organometallic chemistry
7169:Pictet–Spengler reaction
7084:Einhorn–Brunner reaction
7049:Boger pyridine synthesis
6943:Oxo-Diels–Alder reaction
6858:Aza-Diels–Alder reaction
6755:Pictet–Spengler reaction
6655:Hofmann–Löffler reaction
6645:Hegedus indole synthesis
6615:Fischer indole synthesis
6490:Bartoli indole synthesis
6445:Willgerodt rearrangement
6275:McLafferty rearrangement
6185:Ferrier carbocyclization
6000:2,3-Wittig rearrangement
5990:1,2-Wittig rearrangement
5830:Parikh–Doering oxidation
5820:Oxygen rebound mechanism
5485:Adkins–Peterson reaction
5377:Yamaguchi esterification
5317:Hegedus indole synthesis
5282:Bartoli indole synthesis
5153:Bamford–Stevens reaction
5069:Weinreb ketone synthesis
5029:Stork enamine alkylation
4804:Knoevenagel condensation
4674:Ferrier carbocyclization
4564:Castro–Stephens coupling
4190:Hammett acidity function
4180:Free-energy relationship
4125:Curtin–Hammett principle
4110:Conformational isomerism
3627:Organometallic chemistry
3389:Bamford–Stevens reaction
1719:10.1002/ange.19550671610
1331:New Journal of Chemistry
1272:Salt metathesis reaction
383:le Chatelier's Principle
342:Acyclic diene metathesis
314:
132:Nobel Prize in Chemistry
7129:Knorr pyrrole synthesis
7064:Bucherer–Bergs reaction
7009:Allan–Robinson reaction
6988:Wagner-Jauregg reaction
6780:Ring-closing metathesis
6705:Larock indole synthesis
6685:Knorr pyrrole synthesis
6540:Bucherer–Bergs reaction
6405:Stieglitz rearrangement
6385:Skattebøl rearrangement
6355:Ring-closing metathesis
6215:Group transfer reaction
6180:Favorskii rearrangement
6120:Cornforth rearrangement
6050:Bamberger rearrangement
5955:Wolff–Kishner reduction
5775:Markó–Lam deoxygenation
5670:Fleming–Tamao oxidation
5665:Fischer–Tropsch process
5352:Oxymercuration reaction
5332:Knorr pyrrole synthesis
5158:Barton–Kellogg reaction
5064:Wagner-Jauregg reaction
4984:Ring-closing metathesis
4974:Reimer–Tiemann reaction
4964:Rauhut–Currier reaction
4879:Nef isocyanide reaction
4839:Malonic ester synthesis
4809:Knorr pyrrole synthesis
4744:High dilution principle
4679:Friedel–Crafts reaction
4614:Cross-coupling reaction
4539:Bucherer–Bergs reaction
4524:Blanc chloromethylation
4514:Blaise ketone synthesis
4489:Baylis–Hillman reaction
4484:Barton–Kellogg reaction
4459:Allan–Robinson reaction
4365:Woodward–Hoffmann rules
4100:Charge-transfer complex
3788:Half sandwich compounds
3525:Oxymercuration reaction
3394:Barton–Kellogg reaction
2980:Vougioukalakis, G. C.;
1457:10.1515/revce-2017-0003
1300:. Weinheim: Wiley-VCH.
605:Woodward–Hoffmann rules
575:to an equal mixture of
561:molybdenum hexacarbonyl
449:Ziegler–Natta catalysis
330:Ring-closing metathesis
235:heterogeneous catalysts
224:Common Grubbs catalysts
215:Hoveyda–Grubbs catalyst
148:heterogeneous catalysts
7094:Feist–Benary synthesis
6868:Bradsher cycloaddition
6838:4+4 Photocycloaddition
6795:Simmons–Smith reaction
6740:Paternò–Büchi reaction
6600:Feist–Benary synthesis
6590:Dieckmann condensation
6340:Pummerer rearrangement
6320:Oxy-Cope rearrangement
6295:Myers allene synthesis
6245:Jacobsen rearrangement
6160:Electrocyclic reaction
6135:Demjanov rearrangement
6090:Buchner ring expansion
6060:Beckmann rearrangement
6040:Aza-Cope rearrangement
6035:Arndt–Eistert reaction
6010:Alkyne zipper reaction
5930:Transfer hydrogenation
5905:Sharpless oxyamination
5880:Selenoxide elimination
5765:Lombardo methylenation
5690:Griesbaum coozonolysis
5600:Corey–Itsuno reduction
5575:Boyland–Sims oxidation
5515:Angeli–Rimini reaction
5163:Boord olefin synthesis
5107:Arndt–Eistert reaction
5099:Homologation reactions
4899:Nitro-Mannich reaction
4814:Kolbe–Schmitt reaction
4624:Cross-coupling partner
4544:Buchner ring expansion
4464:Arndt–Eistert reaction
4230:Kinetic isotope effect
3977:Rearrangement reaction
3903:Bioinorganic chemistry
3520:Electrophilic addition
3399:Boord olefin synthesis
2928:10.1002/anie.200300576
2874:Cite journal requires
2833:Cite journal requires
2747:Cite journal requires
2460:10.1002/anie.199520391
1788:10.1002/anie.196407231
1684:10.1002/ejoc.200700744
1079:tricyclohexylphosphine
950:
484:titanium tetrachloride
397:
378:
225:
209:isopropoxybenzylidene
202:
142:The reaction requires
79:
7243:Homogeneous catalysis
6953:Pauson–Khand reaction
6790:Sharpless epoxidation
6745:Pechmann condensation
6625:Friedländer synthesis
6575:Davis–Beirut reaction
6430:Wallach rearrangement
6400:Stevens rearrangement
6335:Pinacol rearrangement
6315:Overman rearrangement
6230:Hofmann rearrangement
6225:Hayashi rearrangement
6190:Ferrier rearrangement
6145:Dimroth rearrangement
6130:Curtius rearrangement
6125:Criegee rearrangement
6105:Claisen rearrangement
6095:Carroll rearrangement
6030:Amadori rearrangement
6020:Allylic rearrangement
5900:Sharpless epoxidation
5635:Dess–Martin oxidation
5560:Bohn–Schmidt reaction
5420:Hofmann rearrangement
5223:Kauffmann olefination
5146:Olefination reactions
5084:Wurtz–Fittig reaction
4919:Palladium–NHC complex
4799:Kauffmann olefination
4754:Homologation reaction
4604:Corey–House synthesis
4584:Claisen rearrangement
4380:Yukawa–Tsuno equation
4340:Swain–Lupton equation
4320:Spherical aromaticity
4255:Möbius–Hückel concept
4040:Aromatic ring current
4002:Substitution reaction
3874:Ziegler–Natta process
3778:Metal tetranorbornyls
3444:Kauffmann olefination
1761:U.S. patent 2,721,189
1043:ruthenium trichloride
1017:living polymerization
951:
897:product distribution
893:In this reaction the
852:rate-determining step
765:tungsten hexachloride
624:tungsten hexachloride
565:tungsten hexacarbonyl
395:
376:
323:Cross metathesis (CM)
223:
200:
77:
7248:Industrial processes
7159:Paal–Knorr synthesis
7029:Barton–Zard reaction
6973:Staudinger synthesis
6923:Ketene cycloaddition
6893:Diels–Alder reaction
6873:Cheletropic reaction
6853:Alkyne trimerisation
6735:Paal–Knorr synthesis
6700:Kulinkovich reaction
6675:Jacobsen epoxidation
6595:Diels–Alder reaction
6390:Smiles rearrangement
6380:Sigmatropic reaction
6265:Lossen rearrangement
6115:Corey–Fuchs reaction
6080:Boekelheide reaction
6075:Bergmann degradation
6005:Achmatowicz reaction
5790:Methionine sulfoxide
5590:Clemmensen reduction
5550:Bergmann degradation
5480:Acyloin condensation
5445:Strecker degradation
5400:Bergmann degradation
5367:Ullmann condensation
5233:Peterson olefination
5208:Hydrazone iodination
5188:Elimination reaction
5089:Zincke–Suhl reaction
5009:Sonogashira coupling
4969:Reformatsky reaction
4929:Peterson olefination
4894:Nierenstein reaction
4824:Kulinkovich reaction
4639:Diels–Alder reaction
4599:Corey–Fuchs reaction
4579:Claisen condensation
4449:Alkyne trimerisation
4424:Acyloin condensation
4390:Σ-bishomoaromaticity
4350:Thorpe–Ingold effect
3962:Elimination reaction
3883:Related branches of
3641:Crystal field theory
3565:Diels–Alder reaction
3454:Peterson olefination
3434:Hydrazone iodination
3371:Dehydration reaction
969:methylenecyclohexane
901:
737:homogeneous catalyst
652:chemical equilibrium
535:Herbert S. Eleuterio
426:Thorpe–Ingold effect
362:and thus has a high
296:pharmaceutical drugs
213:to form the related
162:, e.g. combining MCl
7179:Prilezhaev reaction
7164:Pellizzari reaction
6843:(4+3) cycloaddition
6810:Van Leusen reaction
6785:Robinson annulation
6770:Pschorr cyclization
6765:Prilezhaev reaction
6495:Bergman cyclization
6450:Wolff rearrangement
6435:Weerman degradation
6325:Pericyclic reaction
6305:Neber rearrangement
6200:Fries rearrangement
6085:Brook rearrangement
6070:Bergman cyclization
5915:Staudinger reaction
5860:Rosenmund reduction
5850:Reductive amination
5815:Oppenauer oxidation
5605:Corey–Kim oxidation
5580:Cannizzaro reaction
5455:Weerman degradation
5430:Isosaccharinic acid
5342:Mukaiyama hydration
5198:Hofmann elimination
5183:Dehydrohalogenation
5168:Chugaev elimination
4989:Robinson annulation
4934:Pfitzinger reaction
4704:Gattermann reaction
4649:Wulff–Dötz reaction
4629:Dakin–West reaction
4554:Carbonyl allylation
4499:Bergman cyclization
4285:Kennedy J. P. Orton
4205:Hammond's postulate
4175:Flippin–Lodge angle
4145:Electromeric effect
4070:Beta-silicon effect
4055:Baker–Nathan effect
3898:Inorganic chemistry
3717:Migratory insertion
3691:Agostic interaction
3646:Ligand field theory
3424:Hofmann elimination
3404:Chugaev elimination
3362:Dehydrohalogenation
2904:10.1021/ar00173a007
2853:(51). 2002: 34–38.
2812:(51). 2002: 29–33.
2788:10.1021/ja00063a090
2732:10.1021/ja00018a028
2648:10.1021/ja00166a023
2620:10.1021/ja00533a035
2553:10.1021/ja00510a022
2526:10.1021/ja00823a064
2433:10.1021/ja00074a086
2406:10.1021/ja00036a053
2372:10.1021/ja00211a043
2310:1965JPoSL...3.1049R
2256:10.1021/ma00171a053
2248:1987MaMol..20.1169S
2221:10.1021/ja00264a027
2194:10.1021/ja00264a058
2167:10.1021/ja00542a050
2140:10.1021/ja00479a061
2113:10.1021/ja00428a015
2086:10.1021/ja00844a082
2059:10.1021/ja00832a032
2031:10.1021/ja00839a063
2004:10.1021/ic50127a046
1992:Inorganic Chemistry
1977:10.1021/ja00762a073
1950:10.1021/ja00754a067
1911:Tetrahedron Letters
1869:10.1021/ja01017a039
1830:Tetrahedron Letters
1815:10.1021/i360011a002
1746:10.1021/ja01494a057
1711:1955AngCh..67..426Z
1396:10.1021/ar00131a003
1179:Schrock alkylidenes
690:transalkylidenation
443:Historical overview
160:organotin compounds
6928:McCormack reaction
6878:Conia-ene reaction
6710:Madelung synthesis
6500:Biginelli reaction
6290:Mumm rearrangement
6175:Favorskii reaction
6110:Cope rearrangement
6100:Chan rearrangement
5865:Rubottom oxidation
5795:Miyaura borylation
5760:Lipid peroxidation
5755:Lindgren oxidation
5735:Kornblum oxidation
5730:Kolbe electrolysis
5675:Fukuyama reduction
5585:Carbonyl reduction
5435:Marker degradation
5297:Diazonium compound
5287:Boudouard reaction
5266:Carbon-heteroatom
5193:Grieco elimination
4979:Rieche formylation
4924:Passerini reaction
4854:Meerwein arylation
4774:Hydroxymethylation
4669:Favorskii reaction
4569:Chan rearrangement
4504:Biginelli reaction
4429:Aldol condensation
4275:2-Norbornyl cation
4250:Möbius aromaticity
4245:Markovnikov's rule
4140:Effective molarity
4085:Bürgi–Dunitz angle
4075:Bicycloaromaticity
3783:Sandwich compounds
3741:Types of compounds
3666:Isolobal principle
3489:Cope rearrangement
3419:Grieco elimination
3128:10.3762/bjoc.6.124
1623:on 9 December 2011
1077:The corresponding
1047:osmium trichloride
946:
585:reaction mechanism
554:disproportionation
504:reaction mechanism
398:
379:
360:symmetry forbidden
277:1,5-cyclooctadiene
226:
203:
128:Richard R. Schrock
80:
24:Olefin metathesis
7220:
7219:
7216:
7215:
7212:
7211:
7204:Wohl–Aue reaction
6848:6+4 Cycloaddition
6665:Iodolactonization
5985:1,2-rearrangement
5950:Wohl–Aue reaction
5870:Sabatier reaction
5835:Pinnick oxidation
5800:Mozingo reduction
5745:Leuckart reaction
5700:Haloform reaction
5615:Criegee oxidation
5595:Collins oxidation
5545:Benkeser reaction
5540:Bechamp reduction
5510:Andrussow process
5495:Alcohol oxidation
5405:Edman degradation
5312:Haloform reaction
5261:
5260:
5248:Takai olefination
5213:Julia olefination
5039:Takai olefination
4914:Olefin metathesis
4789:Julia olefination
4714:Grignard reaction
4694:Fukuyama coupling
4609:Coupling reaction
4574:Chan–Lam coupling
4444:Alkyne metathesis
4439:Alkane metathesis
4295:Phosphaethynolate
4200:George S. Hammond
4160:Electronic effect
4115:Conjugated system
3997:Stereospecificity
3992:Stereoselectivity
3957:Addition reaction
3946:organic reactions
3911:
3910:
3893:Organic chemistry
3864:Olefin metathesis
3854:Grignard reaction
3753:Grignard reagents
3593:
3592:
3555:Hydrohalogenation
3479:Olefin metathesis
3469:Takai olefination
3439:Julia olefination
3380:Semihydrogenation
3097:(34): 7117–7140.
3073:(18): 4413–4450.
3039:10.1021/ar000114f
2998:10.1021/cr9002424
2965:10.1021/cr800524f
2922:(38): 4592–4633.
2782:(10): 4413–4414.
2726:(18): 6899–6907.
2642:(10): 3875–3886.
2614:(13): 4515–4CF6.
2547:(16): 4558–4570.
2520:(16): 5288–5290.
2499:10.1021/ja952676d
2454:(18): 2039–2041.
2427:(21): 9858–9859.
2400:(10): 3974–3975.
2339:(11): 3097–3115.
2304:(12): 1049–1052.
2161:(22): 6876–6878.
2134:(11): 3611–3613.
2107:(12): 3478–3483.
2080:(11): 3265–3267.
2053:(25): 7808–7809.
1944:(25): 7087–7088.
1863:(15): 4133–4140.
1836:(34): 3327–3329.
1764:(18 October 1955)
1699:Angewandte Chemie
1678:(35): 5909–5916.
1595:10.1021/ja802010d
1589:(21): 6731–6733.
1553:10.1021/jo300766f
1547:(14): 6314–6318.
1518:10.1021/jm9015526
1371:. 5 October 2005.
1367:(Press release).
1315:978-0-471-23896-6
1262:Alkyne metathesis
1257:Alkane metathesis
1142:Ta(CHt−bu)(Ot−bu)
1105:Schrock catalysts
971:switched places:
364:activation energy
263:tungsten trioxide
251:(SHOP) produces (
98:(olefins) by the
88:olefin metathesis
84:organic chemistry
72:
71:
47:olefin-metathesis
7255:
7199:Wenker synthesis
7189:Stollé synthesis
7044:Bobbitt reaction
7014:Auwers synthesis
6958:Povarov reaction
6883:Cyclopropanation
6821:
6820:
6815:Wenker synthesis
6570:Darzens reaction
6520:Bobbitt reaction
6365:Schmidt reaction
6170:Enyne metathesis
5945:Whiting reaction
5940:Wharton reaction
5885:Shapiro reaction
5875:Sarett oxidation
5840:Prévost reaction
5650:Emde degradation
5460:Wohl degradation
5440:Ruff degradation
5410:Emde degradation
5307:Grignard reagent
5243:Shapiro reaction
5228:McMurry reaction
5095:
5094:
5059:Ullmann reaction
5024:Stollé synthesis
5014:Stetter reaction
5004:Shapiro reaction
4994:Sakurai reaction
4889:Negishi coupling
4869:Minisci reaction
4864:Michael reaction
4849:McMurry reaction
4844:Mannich reaction
4724:Hammick reaction
4719:Grignard reagent
4659:Enyne metathesis
4644:Doebner reaction
4634:Darzens reaction
4479:Barbier reaction
4469:Auwers synthesis
4396:
4395:
4370:Woodward's rules
4335:Superaromaticity
4325:Spiroaromaticity
4225:Inductive effect
4220:Hyperconjugation
4195:Hammett equation
4135:Edwards equation
3987:Regioselectivity
3938:
3931:
3924:
3915:
3914:
3859:Monsanto process
3656:d electron count
3651:18-electron rule
3620:
3613:
3606:
3597:
3596:
3535:Cyclopropanation
3464:Shapiro reaction
3449:McMurry reaction
3346:
3329:
3312:
3295:
3278:
3261:
3244:
3227:
3210:
3177:
3170:
3163:
3154:
3153:
3149:
3139:
3106:
3082:
3058:
3017:
2992:(3): 1746–1787.
2986:Chemical Reviews
2976:
2959:(8): 3708–3742.
2953:Chemical Reviews
2947:
2907:
2883:
2877:
2872:
2870:
2862:
2842:
2836:
2831:
2829:
2821:
2792:
2791:
2763:
2757:
2756:
2750:
2745:
2743:
2735:
2658:
2652:
2651:
2630:
2624:
2623:
2590:
2584:
2583:
2563:
2557:
2556:
2536:
2530:
2529:
2509:
2503:
2502:
2470:
2464:
2463:
2443:
2437:
2436:
2416:
2410:
2409:
2391:
2382:
2376:
2375:
2355:
2349:
2348:
2328:
2322:
2321:
2293:
2287:
2286:
2266:
2260:
2259:
2242:(5): 1169–1172.
2231:
2225:
2224:
2204:
2198:
2197:
2177:
2171:
2170:
2150:
2144:
2143:
2123:
2117:
2116:
2096:
2090:
2089:
2069:
2063:
2062:
2041:
2035:
2034:
2025:(6): 1592–1594.
2014:
2008:
2007:
1998:(9): 2166–2170.
1987:
1981:
1980:
1971:(7): 2538–2540.
1960:
1954:
1953:
1933:
1927:
1926:
1906:
1900:
1899:
1879:
1873:
1872:
1852:
1846:
1845:
1825:
1819:
1818:
1798:
1792:
1791:
1771:
1765:
1763:
1756:
1750:
1749:
1740:(9): 2337–2340.
1729:
1723:
1722:
1694:
1688:
1687:
1666:
1660:
1659:
1639:
1633:
1632:
1630:
1628:
1613:
1607:
1606:
1580:
1571:
1565:
1564:
1536:
1530:
1529:
1500:
1494:
1493:
1475:
1469:
1468:
1440:
1431:
1430:
1428:
1426:
1406:
1400:
1399:
1379:
1373:
1372:
1361:
1355:
1354:
1343:10.1039/b412198h
1326:
1320:
1319:
1293:
1267:Enyne metathesis
1228:
1216:
1207:
1174:
1166:W(O)(CHt−Bu)(Cl)
1158:cyclopentadienyl
1147:
1132:
1119:
1115:CpTa(=CH−t−Bu)Cl
1073:
1039:Robert H. Grubbs
1032:Grubbs catalysts
1026:functional group
1011:
991:
979:
955:
953:
952:
947:
942:
941:
929:
928:
916:
915:
889:
877:
865:
846:
816:
805:Robert H. Grubbs
790:
754:
723:
707:
692:mechanism and a
646:
599:
569:molybdenum oxide
525:
494:
184:Grubbs catalysts
172:catalyst support
124:Robert H. Grubbs
112:hazardous wastes
92:organic reaction
64:
49:
21:
20:
7263:
7262:
7258:
7257:
7256:
7254:
7253:
7252:
7223:
7222:
7221:
7208:
7109:Gewald reaction
6992:
6819:
6800:Skraup reaction
6635:Graham reaction
6630:Gewald reaction
6461:
6454:
5976:
5969:
5925:Swern oxidation
5910:Stahl oxidation
5855:Riley oxidation
5810:Omega oxidation
5770:Luche reduction
5720:Jones oxidation
5685:Glycol cleavage
5680:Ganem oxidation
5625:Davis oxidation
5620:Dakin oxidation
5555:Birch reduction
5505:Amide reduction
5471:
5464:
5425:Hooker reaction
5387:
5381:
5269:
5267:
5257:
5253:Wittig reaction
5141:
5137:Wittig reaction
5112:Hooker reaction
5093:
5074:Wittig reaction
5049:Thorpe reaction
5034:Suzuki reaction
5019:Stille reaction
4954:Quelet reaction
4829:Kumada coupling
4779:Ivanov reaction
4769:Hydrovinylation
4749:Hiyama coupling
4709:Glaser coupling
4519:Blaise reaction
4509:Bingel reaction
4494:Benary reaction
4411:
4409:
4403:
4394:
4290:Passive binding
4210:Homoaromaticity
4060:Baldwin's rules
4035:Antiaromaticity
4030:Anomeric effect
4006:
3948:
3942:
3912:
3907:
3878:
3832:
3748:Gilman reagents
3736:
3732:Carbometalation
3727:Transmetalation
3700:
3629:
3624:
3594:
3589:
3575:Dehydrogenation
3545:Dihydroxylation
3493:
3474:Wittig reaction
3350:
3345:
3341:
3337:
3328:
3324:
3320:
3311:
3307:
3303:
3294:
3290:
3286:
3277:
3273:
3269:
3260:
3256:
3252:
3243:
3239:
3235:
3226:
3222:
3218:
3209:
3205:
3201:
3186:
3181:
2875:
2873:
2864:
2863:
2845:
2834:
2832:
2823:
2822:
2804:
2801:
2799:Further reading
2796:
2795:
2773:
2769:
2764:
2760:
2748:
2746:
2737:
2736:
2721:
2717:
2713:
2709:
2701:
2697:
2693:
2689:
2681:
2673:
2669:
2665:
2659:
2655:
2631:
2627:
2605:
2601:
2597:
2591:
2587:
2564:
2560:
2537:
2533:
2510:
2506:
2484:
2480:
2476:
2471:
2467:
2444:
2440:
2417:
2413:
2389:
2383:
2379:
2356:
2352:
2329:
2325:
2294:
2290:
2267:
2263:
2232:
2228:
2205:
2201:
2178:
2174:
2151:
2147:
2124:
2120:
2097:
2093:
2070:
2066:
2042:
2038:
2015:
2011:
1988:
1984:
1961:
1957:
1934:
1930:
1917:(11): 789–793.
1907:
1903:
1880:
1876:
1853:
1849:
1826:
1822:
1799:
1795:
1782:(11): 723–729.
1772:
1768:
1759:
1757:
1753:
1730:
1726:
1695:
1691:
1667:
1663:
1640:
1636:
1626:
1624:
1615:
1614:
1610:
1578:
1572:
1568:
1537:
1533:
1501:
1497:
1490:
1476:
1472:
1441:
1434:
1424:
1422:
1407:
1403:
1390:(11): 342–348.
1380:
1376:
1363:
1362:
1358:
1327:
1323:
1316:
1294:
1285:
1280:
1253:
1206:
1202:
1198:
1194:
1190:
1186:
1182:
1173:
1169:
1165:
1162:organophosphine
1145:
1141:
1137:
1118:
1114:
1107:
1099:Grubbs catalyst
1096:
1092:
1088:
1084:
1064:
1060:
1056:
1052:
1034:
997:total synthesis
937:
933:
924:
920:
911:
907:
902:
899:
898:
796:carbon monoxide
695:transalkylation
687:
683:
679:
637:
634:compound EtAlMe
612:Nissim Calderon
445:
356:
317:
305:
290:
286:
231:
169:
165:
156:organoaluminium
153:
144:metal catalysts
140:
60:
45:
17:
12:
11:
5:
7261:
7251:
7250:
7245:
7240:
7235:
7218:
7217:
7214:
7213:
7210:
7209:
7207:
7206:
7201:
7196:
7191:
7186:
7181:
7176:
7171:
7166:
7161:
7156:
7151:
7146:
7141:
7136:
7131:
7126:
7121:
7116:
7114:Hantzsch ester
7111:
7106:
7101:
7096:
7091:
7086:
7081:
7076:
7071:
7066:
7061:
7056:
7051:
7046:
7041:
7036:
7031:
7026:
7024:Banert cascade
7021:
7016:
7011:
7006:
7000:
6998:
6994:
6993:
6991:
6990:
6985:
6980:
6975:
6970:
6965:
6963:Prato reaction
6960:
6955:
6950:
6945:
6940:
6935:
6930:
6925:
6920:
6915:
6910:
6905:
6900:
6895:
6890:
6885:
6880:
6875:
6870:
6865:
6860:
6855:
6850:
6845:
6840:
6835:
6829:
6827:
6818:
6817:
6812:
6807:
6802:
6797:
6792:
6787:
6782:
6777:
6772:
6767:
6762:
6757:
6752:
6747:
6742:
6737:
6732:
6727:
6722:
6717:
6712:
6707:
6702:
6697:
6692:
6687:
6682:
6677:
6672:
6667:
6662:
6657:
6652:
6647:
6642:
6637:
6632:
6627:
6622:
6617:
6612:
6607:
6602:
6597:
6592:
6587:
6582:
6577:
6572:
6567:
6562:
6557:
6552:
6547:
6542:
6537:
6532:
6527:
6522:
6517:
6512:
6507:
6502:
6497:
6492:
6487:
6482:
6477:
6472:
6466:
6464:
6456:
6455:
6453:
6452:
6447:
6442:
6437:
6432:
6427:
6422:
6417:
6412:
6407:
6402:
6397:
6392:
6387:
6382:
6377:
6372:
6367:
6362:
6357:
6352:
6347:
6342:
6337:
6332:
6327:
6322:
6317:
6312:
6307:
6302:
6297:
6292:
6287:
6282:
6277:
6272:
6267:
6262:
6257:
6252:
6247:
6242:
6237:
6232:
6227:
6222:
6217:
6212:
6207:
6202:
6197:
6192:
6187:
6182:
6177:
6172:
6167:
6162:
6157:
6152:
6147:
6142:
6137:
6132:
6127:
6122:
6117:
6112:
6107:
6102:
6097:
6092:
6087:
6082:
6077:
6072:
6067:
6062:
6057:
6055:Banert cascade
6052:
6047:
6042:
6037:
6032:
6027:
6022:
6017:
6012:
6007:
6002:
5997:
5992:
5987:
5981:
5979:
5975:Rearrangement
5971:
5970:
5968:
5967:
5965:Zinin reaction
5962:
5957:
5952:
5947:
5942:
5937:
5935:Wacker process
5932:
5927:
5922:
5917:
5912:
5907:
5902:
5897:
5892:
5887:
5882:
5877:
5872:
5867:
5862:
5857:
5852:
5847:
5842:
5837:
5832:
5827:
5822:
5817:
5812:
5807:
5802:
5797:
5792:
5787:
5782:
5777:
5772:
5767:
5762:
5757:
5752:
5747:
5742:
5737:
5732:
5727:
5722:
5717:
5712:
5710:Hydrogenolysis
5707:
5702:
5697:
5692:
5687:
5682:
5677:
5672:
5667:
5662:
5660:Étard reaction
5657:
5652:
5647:
5642:
5637:
5632:
5627:
5622:
5617:
5612:
5607:
5602:
5597:
5592:
5587:
5582:
5577:
5572:
5567:
5565:Bosch reaction
5562:
5557:
5552:
5547:
5542:
5537:
5532:
5527:
5522:
5517:
5512:
5507:
5502:
5497:
5492:
5487:
5482:
5476:
5474:
5470:Organic redox
5466:
5465:
5463:
5462:
5457:
5452:
5447:
5442:
5437:
5432:
5427:
5422:
5417:
5412:
5407:
5402:
5397:
5391:
5389:
5383:
5382:
5380:
5379:
5374:
5369:
5364:
5359:
5354:
5349:
5344:
5339:
5334:
5329:
5324:
5319:
5314:
5309:
5304:
5302:Esterification
5299:
5294:
5289:
5284:
5279:
5273:
5271:
5263:
5262:
5259:
5258:
5256:
5255:
5250:
5245:
5240:
5235:
5230:
5225:
5220:
5215:
5210:
5205:
5200:
5195:
5190:
5185:
5180:
5175:
5170:
5165:
5160:
5155:
5149:
5147:
5143:
5142:
5140:
5139:
5134:
5129:
5124:
5119:
5114:
5109:
5103:
5101:
5092:
5091:
5086:
5081:
5079:Wurtz reaction
5076:
5071:
5066:
5061:
5056:
5051:
5046:
5041:
5036:
5031:
5026:
5021:
5016:
5011:
5006:
5001:
4996:
4991:
4986:
4981:
4976:
4971:
4966:
4961:
4956:
4951:
4949:Prins reaction
4946:
4941:
4936:
4931:
4926:
4921:
4916:
4911:
4906:
4901:
4896:
4891:
4886:
4881:
4876:
4871:
4866:
4861:
4856:
4851:
4846:
4841:
4836:
4831:
4826:
4821:
4816:
4811:
4806:
4801:
4796:
4791:
4786:
4781:
4776:
4771:
4766:
4764:Hydrocyanation
4761:
4756:
4751:
4746:
4741:
4736:
4734:Henry reaction
4731:
4726:
4721:
4716:
4711:
4706:
4701:
4696:
4691:
4686:
4681:
4676:
4671:
4666:
4661:
4656:
4651:
4646:
4641:
4636:
4631:
4626:
4621:
4616:
4611:
4606:
4601:
4596:
4591:
4586:
4581:
4576:
4571:
4566:
4561:
4556:
4551:
4546:
4541:
4536:
4531:
4526:
4521:
4516:
4511:
4506:
4501:
4496:
4491:
4486:
4481:
4476:
4471:
4466:
4461:
4456:
4451:
4446:
4441:
4436:
4434:Aldol reaction
4431:
4426:
4421:
4415:
4413:
4408:Carbon-carbon
4405:
4404:
4393:
4392:
4387:
4385:Zaitsev's rule
4382:
4377:
4372:
4367:
4362:
4357:
4352:
4347:
4342:
4337:
4332:
4330:Steric effects
4327:
4322:
4317:
4312:
4307:
4302:
4297:
4292:
4287:
4282:
4277:
4272:
4267:
4262:
4257:
4252:
4247:
4242:
4237:
4232:
4227:
4222:
4217:
4212:
4207:
4202:
4197:
4192:
4187:
4182:
4177:
4172:
4167:
4162:
4157:
4152:
4147:
4142:
4137:
4132:
4127:
4122:
4117:
4112:
4107:
4102:
4097:
4092:
4087:
4082:
4077:
4072:
4067:
4062:
4057:
4052:
4047:
4042:
4037:
4032:
4027:
4022:
4017:
4011:
4008:
4007:
4005:
4004:
3999:
3994:
3989:
3984:
3982:Redox reaction
3979:
3974:
3969:
3967:Polymerization
3964:
3959:
3953:
3950:
3949:
3941:
3940:
3933:
3926:
3918:
3909:
3908:
3906:
3905:
3900:
3895:
3889:
3887:
3880:
3879:
3877:
3876:
3871:
3866:
3861:
3856:
3851:
3849:Cativa process
3846:
3840:
3838:
3834:
3833:
3831:
3830:
3825:
3820:
3815:
3810:
3805:
3800:
3795:
3790:
3785:
3780:
3775:
3770:
3765:
3760:
3755:
3750:
3744:
3742:
3738:
3737:
3735:
3734:
3729:
3724:
3719:
3714:
3708:
3706:
3702:
3701:
3699:
3698:
3693:
3688:
3683:
3678:
3673:
3668:
3663:
3658:
3653:
3648:
3643:
3637:
3635:
3631:
3630:
3623:
3622:
3615:
3608:
3600:
3591:
3590:
3588:
3587:
3582:
3577:
3572:
3570:Wacker process
3567:
3562:
3560:Polymerization
3557:
3552:
3547:
3542:
3537:
3532:
3527:
3522:
3517:
3512:
3507:
3501:
3499:
3495:
3494:
3492:
3491:
3486:
3481:
3476:
3471:
3466:
3461:
3456:
3451:
3446:
3441:
3436:
3431:
3426:
3421:
3416:
3411:
3406:
3401:
3396:
3391:
3386:
3377:
3368:
3358:
3356:
3352:
3351:
3349:
3348:
3343:
3339:
3331:
3326:
3322:
3314:
3309:
3305:
3297:
3292:
3288:
3280:
3275:
3271:
3263:
3258:
3254:
3246:
3241:
3237:
3229:
3224:
3220:
3212:
3207:
3203:
3194:
3192:
3188:
3187:
3180:
3179:
3172:
3165:
3157:
3151:
3150:
3107:
3083:
3059:
3021:Trnka, T. M.;
3018:
2977:
2948:
2912:Schrock, R. R.
2908:
2898:(5): 158–165.
2888:Schrock, R. R.
2884:
2876:|journal=
2843:
2835:|journal=
2800:
2797:
2794:
2793:
2771:
2767:
2758:
2749:|journal=
2719:
2715:
2711:
2707:
2699:
2695:
2691:
2687:
2679:
2671:
2667:
2663:
2653:
2625:
2603:
2599:
2595:
2585:
2574:(1–3): 73–83.
2558:
2531:
2504:
2482:
2478:
2474:
2465:
2438:
2411:
2377:
2366:(3): 960–961.
2350:
2323:
2288:
2277:(3): 895–905.
2261:
2236:Macromolecules
2226:
2215:(4): 733–742.
2199:
2188:(4): 855–856.
2172:
2145:
2118:
2091:
2064:
2036:
2009:
1982:
1955:
1928:
1901:
1890:(1): 161–176.
1874:
1847:
1820:
1809:(3): 170–173.
1793:
1766:
1751:
1724:
1689:
1661:
1650:(1): 161–176.
1634:
1608:
1566:
1531:
1512:(6): 2443–63.
1495:
1488:
1470:
1451:(5): 595–655.
1432:
1421:on 12 May 2006
1401:
1374:
1369:Nobelprize.org
1356:
1321:
1314:
1282:
1281:
1279:
1276:
1275:
1274:
1269:
1264:
1259:
1252:
1249:
1230:
1229:
1218:
1217:
1204:
1200:
1196:
1192:
1188:
1184:
1183:Mo(NAr)(CHC(CH
1171:
1167:
1143:
1139:
1134:
1133:
1116:
1106:
1103:
1094:
1090:
1086:
1082:
1075:
1074:
1062:
1058:
1054:
1050:
1033:
1030:
1013:
1012:
993:
992:
981:
980:
945:
940:
936:
932:
927:
923:
919:
914:
910:
906:
891:
890:
879:
878:
867:
866:
848:
847:
818:
817:
800:metal carbonyl
792:
791:
772:cyclobutadiene
756:
755:
725:
724:
709:
708:
685:
681:
677:
648:
647:
635:
632:organoaluminum
601:
600:
527:
526:
496:
495:
476:polynorbornene
444:
441:
437:Wittig reagent
355:
352:
351:
350:
345:
339:
333:
327:
324:
316:
313:
304:
301:
300:
299:
292:
288:
284:
270:
256:
246:
230:
227:
180:organometallic
167:
163:
151:
139:
136:
70:
69:
66:
65:
58:
51:
50:
43:
39:
38:
34:
33:
30:
29:Reaction type
26:
25:
15:
9:
6:
4:
3:
2:
7260:
7249:
7246:
7244:
7241:
7239:
7236:
7234:
7231:
7230:
7228:
7205:
7202:
7200:
7197:
7195:
7192:
7190:
7187:
7185:
7182:
7180:
7177:
7175:
7172:
7170:
7167:
7165:
7162:
7160:
7157:
7155:
7152:
7150:
7147:
7145:
7142:
7140:
7137:
7135:
7132:
7130:
7127:
7125:
7124:Herz reaction
7122:
7120:
7117:
7115:
7112:
7110:
7107:
7105:
7102:
7100:
7097:
7095:
7092:
7090:
7087:
7085:
7082:
7080:
7077:
7075:
7072:
7070:
7067:
7065:
7062:
7060:
7057:
7055:
7052:
7050:
7047:
7045:
7042:
7040:
7037:
7035:
7032:
7030:
7027:
7025:
7022:
7020:
7017:
7015:
7012:
7010:
7007:
7005:
7002:
7001:
6999:
6995:
6989:
6986:
6984:
6981:
6979:
6976:
6974:
6971:
6969:
6966:
6964:
6961:
6959:
6956:
6954:
6951:
6949:
6946:
6944:
6941:
6939:
6936:
6934:
6931:
6929:
6926:
6924:
6921:
6919:
6916:
6914:
6911:
6909:
6906:
6904:
6901:
6899:
6896:
6894:
6891:
6889:
6886:
6884:
6881:
6879:
6876:
6874:
6871:
6869:
6866:
6864:
6861:
6859:
6856:
6854:
6851:
6849:
6846:
6844:
6841:
6839:
6836:
6834:
6831:
6830:
6828:
6826:
6825:Cycloaddition
6822:
6816:
6813:
6811:
6808:
6806:
6803:
6801:
6798:
6796:
6793:
6791:
6788:
6786:
6783:
6781:
6778:
6776:
6773:
6771:
6768:
6766:
6763:
6761:
6758:
6756:
6753:
6751:
6748:
6746:
6743:
6741:
6738:
6736:
6733:
6731:
6728:
6726:
6723:
6721:
6718:
6716:
6713:
6711:
6708:
6706:
6703:
6701:
6698:
6696:
6693:
6691:
6688:
6686:
6683:
6681:
6678:
6676:
6673:
6671:
6670:Isay reaction
6668:
6666:
6663:
6661:
6658:
6656:
6653:
6651:
6648:
6646:
6643:
6641:
6638:
6636:
6633:
6631:
6628:
6626:
6623:
6621:
6618:
6616:
6613:
6611:
6608:
6606:
6603:
6601:
6598:
6596:
6593:
6591:
6588:
6586:
6583:
6581:
6578:
6576:
6573:
6571:
6568:
6566:
6565:Cycloaddition
6563:
6561:
6558:
6556:
6553:
6551:
6548:
6546:
6543:
6541:
6538:
6536:
6533:
6531:
6528:
6526:
6523:
6521:
6518:
6516:
6513:
6511:
6508:
6506:
6503:
6501:
6498:
6496:
6493:
6491:
6488:
6486:
6483:
6481:
6478:
6476:
6473:
6471:
6468:
6467:
6465:
6463:
6460:Ring forming
6457:
6451:
6448:
6446:
6443:
6441:
6438:
6436:
6433:
6431:
6428:
6426:
6423:
6421:
6418:
6416:
6413:
6411:
6408:
6406:
6403:
6401:
6398:
6396:
6393:
6391:
6388:
6386:
6383:
6381:
6378:
6376:
6373:
6371:
6368:
6366:
6363:
6361:
6360:Rupe reaction
6358:
6356:
6353:
6351:
6348:
6346:
6343:
6341:
6338:
6336:
6333:
6331:
6328:
6326:
6323:
6321:
6318:
6316:
6313:
6311:
6308:
6306:
6303:
6301:
6298:
6296:
6293:
6291:
6288:
6286:
6283:
6281:
6278:
6276:
6273:
6271:
6268:
6266:
6263:
6261:
6258:
6256:
6253:
6251:
6248:
6246:
6243:
6241:
6238:
6236:
6233:
6231:
6228:
6226:
6223:
6221:
6218:
6216:
6213:
6211:
6208:
6206:
6203:
6201:
6198:
6196:
6193:
6191:
6188:
6186:
6183:
6181:
6178:
6176:
6173:
6171:
6168:
6166:
6163:
6161:
6158:
6156:
6153:
6151:
6148:
6146:
6143:
6141:
6138:
6136:
6133:
6131:
6128:
6126:
6123:
6121:
6118:
6116:
6113:
6111:
6108:
6106:
6103:
6101:
6098:
6096:
6093:
6091:
6088:
6086:
6083:
6081:
6078:
6076:
6073:
6071:
6068:
6066:
6063:
6061:
6058:
6056:
6053:
6051:
6048:
6046:
6043:
6041:
6038:
6036:
6033:
6031:
6028:
6026:
6023:
6021:
6018:
6016:
6013:
6011:
6008:
6006:
6003:
6001:
5998:
5996:
5993:
5991:
5988:
5986:
5983:
5982:
5980:
5978:
5972:
5966:
5963:
5961:
5958:
5956:
5953:
5951:
5948:
5946:
5943:
5941:
5938:
5936:
5933:
5931:
5928:
5926:
5923:
5921:
5918:
5916:
5913:
5911:
5908:
5906:
5903:
5901:
5898:
5896:
5893:
5891:
5888:
5886:
5883:
5881:
5878:
5876:
5873:
5871:
5868:
5866:
5863:
5861:
5858:
5856:
5853:
5851:
5848:
5846:
5843:
5841:
5838:
5836:
5833:
5831:
5828:
5826:
5823:
5821:
5818:
5816:
5813:
5811:
5808:
5806:
5803:
5801:
5798:
5796:
5793:
5791:
5788:
5786:
5783:
5781:
5778:
5776:
5773:
5771:
5768:
5766:
5763:
5761:
5758:
5756:
5753:
5751:
5750:Ley oxidation
5748:
5746:
5743:
5741:
5738:
5736:
5733:
5731:
5728:
5726:
5723:
5721:
5718:
5716:
5715:Hydroxylation
5713:
5711:
5708:
5706:
5705:Hydrogenation
5703:
5701:
5698:
5696:
5693:
5691:
5688:
5686:
5683:
5681:
5678:
5676:
5673:
5671:
5668:
5666:
5663:
5661:
5658:
5656:
5653:
5651:
5648:
5646:
5643:
5641:
5640:DNA oxidation
5638:
5636:
5633:
5631:
5630:Deoxygenation
5628:
5626:
5623:
5621:
5618:
5616:
5613:
5611:
5608:
5606:
5603:
5601:
5598:
5596:
5593:
5591:
5588:
5586:
5583:
5581:
5578:
5576:
5573:
5571:
5568:
5566:
5563:
5561:
5558:
5556:
5553:
5551:
5548:
5546:
5543:
5541:
5538:
5536:
5533:
5531:
5528:
5526:
5523:
5521:
5520:Aromatization
5518:
5516:
5513:
5511:
5508:
5506:
5503:
5501:
5498:
5496:
5493:
5491:
5488:
5486:
5483:
5481:
5478:
5477:
5475:
5473:
5467:
5461:
5458:
5456:
5453:
5451:
5448:
5446:
5443:
5441:
5438:
5436:
5433:
5431:
5428:
5426:
5423:
5421:
5418:
5416:
5413:
5411:
5408:
5406:
5403:
5401:
5398:
5396:
5393:
5392:
5390:
5384:
5378:
5375:
5373:
5370:
5368:
5365:
5363:
5360:
5358:
5357:Reed reaction
5355:
5353:
5350:
5348:
5345:
5343:
5340:
5338:
5335:
5333:
5330:
5328:
5325:
5323:
5320:
5318:
5315:
5313:
5310:
5308:
5305:
5303:
5300:
5298:
5295:
5293:
5290:
5288:
5285:
5283:
5280:
5278:
5275:
5274:
5272:
5268:bond forming
5264:
5254:
5251:
5249:
5246:
5244:
5241:
5239:
5236:
5234:
5231:
5229:
5226:
5224:
5221:
5219:
5216:
5214:
5211:
5209:
5206:
5204:
5201:
5199:
5196:
5194:
5191:
5189:
5186:
5184:
5181:
5179:
5176:
5174:
5173:Cope reaction
5171:
5169:
5166:
5164:
5161:
5159:
5156:
5154:
5151:
5150:
5148:
5144:
5138:
5135:
5133:
5130:
5128:
5125:
5123:
5120:
5118:
5115:
5113:
5110:
5108:
5105:
5104:
5102:
5100:
5096:
5090:
5087:
5085:
5082:
5080:
5077:
5075:
5072:
5070:
5067:
5065:
5062:
5060:
5057:
5055:
5052:
5050:
5047:
5045:
5042:
5040:
5037:
5035:
5032:
5030:
5027:
5025:
5022:
5020:
5017:
5015:
5012:
5010:
5007:
5005:
5002:
5000:
4997:
4995:
4992:
4990:
4987:
4985:
4982:
4980:
4977:
4975:
4972:
4970:
4967:
4965:
4962:
4960:
4957:
4955:
4952:
4950:
4947:
4945:
4942:
4940:
4937:
4935:
4932:
4930:
4927:
4925:
4922:
4920:
4917:
4915:
4912:
4910:
4907:
4905:
4902:
4900:
4897:
4895:
4892:
4890:
4887:
4885:
4884:Nef synthesis
4882:
4880:
4877:
4875:
4872:
4870:
4867:
4865:
4862:
4860:
4859:Methylenation
4857:
4855:
4852:
4850:
4847:
4845:
4842:
4840:
4837:
4835:
4832:
4830:
4827:
4825:
4822:
4820:
4817:
4815:
4812:
4810:
4807:
4805:
4802:
4800:
4797:
4795:
4792:
4790:
4787:
4785:
4782:
4780:
4777:
4775:
4772:
4770:
4767:
4765:
4762:
4760:
4757:
4755:
4752:
4750:
4747:
4745:
4742:
4740:
4737:
4735:
4732:
4730:
4729:Heck reaction
4727:
4725:
4722:
4720:
4717:
4715:
4712:
4710:
4707:
4705:
4702:
4700:
4697:
4695:
4692:
4690:
4687:
4685:
4682:
4680:
4677:
4675:
4672:
4670:
4667:
4665:
4662:
4660:
4657:
4655:
4652:
4650:
4647:
4645:
4642:
4640:
4637:
4635:
4632:
4630:
4627:
4625:
4622:
4620:
4617:
4615:
4612:
4610:
4607:
4605:
4602:
4600:
4597:
4595:
4592:
4590:
4587:
4585:
4582:
4580:
4577:
4575:
4572:
4570:
4567:
4565:
4562:
4560:
4557:
4555:
4552:
4550:
4547:
4545:
4542:
4540:
4537:
4535:
4532:
4530:
4527:
4525:
4522:
4520:
4517:
4515:
4512:
4510:
4507:
4505:
4502:
4500:
4497:
4495:
4492:
4490:
4487:
4485:
4482:
4480:
4477:
4475:
4472:
4470:
4467:
4465:
4462:
4460:
4457:
4455:
4452:
4450:
4447:
4445:
4442:
4440:
4437:
4435:
4432:
4430:
4427:
4425:
4422:
4420:
4417:
4416:
4414:
4410:bond forming
4406:
4402:
4397:
4391:
4388:
4386:
4383:
4381:
4378:
4376:
4375:Y-aromaticity
4373:
4371:
4368:
4366:
4363:
4361:
4360:Walsh diagram
4358:
4356:
4353:
4351:
4348:
4346:
4345:Taft equation
4343:
4341:
4338:
4336:
4333:
4331:
4328:
4326:
4323:
4321:
4318:
4316:
4315:Σ-aromaticity
4313:
4311:
4308:
4306:
4303:
4301:
4298:
4296:
4293:
4291:
4288:
4286:
4283:
4281:
4278:
4276:
4273:
4271:
4268:
4266:
4263:
4261:
4258:
4256:
4253:
4251:
4248:
4246:
4243:
4241:
4240:Marcus theory
4238:
4236:
4233:
4231:
4228:
4226:
4223:
4221:
4218:
4216:
4215:Hückel's rule
4213:
4211:
4208:
4206:
4203:
4201:
4198:
4196:
4193:
4191:
4188:
4186:
4183:
4181:
4178:
4176:
4173:
4171:
4170:Evelyn effect
4168:
4166:
4163:
4161:
4158:
4156:
4153:
4151:
4150:Electron-rich
4148:
4146:
4143:
4141:
4138:
4136:
4133:
4131:
4128:
4126:
4123:
4121:
4118:
4116:
4113:
4111:
4108:
4106:
4103:
4101:
4098:
4096:
4093:
4091:
4088:
4086:
4083:
4081:
4078:
4076:
4073:
4071:
4068:
4066:
4065:Bema Hapothle
4063:
4061:
4058:
4056:
4053:
4051:
4048:
4046:
4043:
4041:
4038:
4036:
4033:
4031:
4028:
4026:
4023:
4021:
4018:
4016:
4013:
4012:
4009:
4003:
4000:
3998:
3995:
3993:
3990:
3988:
3985:
3983:
3980:
3978:
3975:
3973:
3970:
3968:
3965:
3963:
3960:
3958:
3955:
3954:
3951:
3947:
3939:
3934:
3932:
3927:
3925:
3920:
3919:
3916:
3904:
3901:
3899:
3896:
3894:
3891:
3890:
3888:
3886:
3881:
3875:
3872:
3870:
3867:
3865:
3862:
3860:
3857:
3855:
3852:
3850:
3847:
3845:
3844:Carbonylation
3842:
3841:
3839:
3835:
3829:
3826:
3824:
3821:
3819:
3816:
3814:
3811:
3809:
3806:
3804:
3801:
3799:
3796:
3794:
3791:
3789:
3786:
3784:
3781:
3779:
3776:
3774:
3771:
3769:
3766:
3764:
3761:
3759:
3756:
3754:
3751:
3749:
3746:
3745:
3743:
3739:
3733:
3730:
3728:
3725:
3723:
3720:
3718:
3715:
3713:
3710:
3709:
3707:
3703:
3697:
3694:
3692:
3689:
3687:
3684:
3682:
3679:
3677:
3674:
3672:
3671:π backbonding
3669:
3667:
3664:
3662:
3659:
3657:
3654:
3652:
3649:
3647:
3644:
3642:
3639:
3638:
3636:
3632:
3628:
3621:
3616:
3614:
3609:
3607:
3602:
3601:
3598:
3586:
3583:
3581:
3578:
3576:
3573:
3571:
3568:
3566:
3563:
3561:
3558:
3556:
3553:
3551:
3548:
3546:
3543:
3541:
3538:
3536:
3533:
3531:
3530:Hydroboration
3528:
3526:
3523:
3521:
3518:
3516:
3513:
3511:
3508:
3506:
3505:Hydrogenation
3503:
3502:
3500:
3496:
3490:
3487:
3485:
3482:
3480:
3477:
3475:
3472:
3470:
3467:
3465:
3462:
3460:
3457:
3455:
3452:
3450:
3447:
3445:
3442:
3440:
3437:
3435:
3432:
3430:
3427:
3425:
3422:
3420:
3417:
3415:
3412:
3410:
3409:Cope reaction
3407:
3405:
3402:
3400:
3397:
3395:
3392:
3390:
3387:
3385:
3381:
3378:
3376:
3372:
3369:
3367:
3363:
3360:
3359:
3357:
3353:
3335:
3332:
3318:
3315:
3301:
3298:
3284:
3281:
3267:
3264:
3250:
3247:
3233:
3230:
3216:
3213:
3199:
3196:
3195:
3193:
3189:
3185:
3178:
3173:
3171:
3166:
3164:
3159:
3158:
3155:
3147:
3143:
3138:
3133:
3129:
3125:
3122:: 1089–1090.
3121:
3117:
3113:
3108:
3104:
3100:
3096:
3092:
3088:
3087:Grubbs, R. H.
3084:
3080:
3076:
3072:
3068:
3064:
3063:Grubbs, R. H.
3060:
3056:
3052:
3048:
3044:
3040:
3036:
3032:
3028:
3024:
3023:Grubbs, R. H.
3019:
3015:
3011:
3007:
3003:
2999:
2995:
2991:
2987:
2983:
2982:Grubbs, R. H.
2978:
2974:
2970:
2966:
2962:
2958:
2954:
2949:
2945:
2941:
2937:
2933:
2929:
2925:
2921:
2917:
2913:
2909:
2905:
2901:
2897:
2893:
2889:
2885:
2881:
2868:
2860:
2856:
2852:
2848:
2844:
2840:
2827:
2819:
2815:
2811:
2807:
2803:
2802:
2789:
2785:
2781:
2777:
2762:
2754:
2741:
2733:
2729:
2725:
2705:
2685:
2677:
2657:
2649:
2645:
2641:
2637:
2629:
2621:
2617:
2613:
2609:
2589:
2581:
2577:
2573:
2569:
2562:
2554:
2550:
2546:
2542:
2535:
2527:
2523:
2519:
2515:
2508:
2500:
2496:
2492:
2488:
2469:
2461:
2457:
2453:
2449:
2442:
2434:
2430:
2426:
2422:
2415:
2407:
2403:
2399:
2395:
2388:
2381:
2373:
2369:
2365:
2361:
2354:
2346:
2342:
2338:
2334:
2327:
2319:
2315:
2311:
2307:
2303:
2299:
2292:
2284:
2280:
2276:
2272:
2265:
2257:
2253:
2249:
2245:
2241:
2237:
2230:
2222:
2218:
2214:
2210:
2203:
2195:
2191:
2187:
2183:
2176:
2168:
2164:
2160:
2156:
2149:
2141:
2137:
2133:
2129:
2122:
2114:
2110:
2106:
2102:
2095:
2087:
2083:
2079:
2075:
2068:
2060:
2056:
2052:
2048:
2040:
2032:
2028:
2024:
2020:
2013:
2005:
2001:
1997:
1993:
1986:
1978:
1974:
1970:
1966:
1959:
1951:
1947:
1943:
1939:
1932:
1924:
1920:
1916:
1912:
1905:
1897:
1893:
1889:
1885:
1878:
1870:
1866:
1862:
1858:
1851:
1843:
1839:
1835:
1831:
1824:
1816:
1812:
1808:
1804:
1797:
1789:
1785:
1781:
1777:
1770:
1762:
1755:
1747:
1743:
1739:
1735:
1728:
1720:
1716:
1712:
1708:
1704:
1700:
1693:
1685:
1681:
1677:
1673:
1665:
1657:
1653:
1649:
1646:(in French).
1645:
1638:
1622:
1618:
1612:
1604:
1600:
1596:
1592:
1588:
1584:
1577:
1570:
1562:
1558:
1554:
1550:
1546:
1542:
1535:
1527:
1523:
1519:
1515:
1511:
1507:
1499:
1491:
1489:3-527-28838-4
1485:
1481:
1474:
1466:
1462:
1458:
1454:
1450:
1446:
1439:
1437:
1420:
1416:
1412:
1405:
1397:
1393:
1389:
1385:
1378:
1370:
1366:
1360:
1352:
1348:
1344:
1340:
1336:
1332:
1325:
1317:
1311:
1307:
1303:
1299:
1292:
1290:
1288:
1283:
1273:
1270:
1268:
1265:
1263:
1260:
1258:
1255:
1254:
1248:
1246:
1242:
1239:
1238:norbornadiene
1235:
1227:
1223:
1222:
1221:
1215:
1211:
1210:
1209:
1180:
1176:
1163:
1159:
1155:
1151:
1131:
1127:
1126:
1125:
1123:
1112:
1102:
1100:
1080:
1072:
1068:
1067:
1066:
1048:
1044:
1040:
1029:
1027:
1022:
1018:
1010:
1006:
1005:
1004:
1002:
998:
990:
986:
985:
984:
978:
974:
973:
972:
970:
966:
962:
961:Tebbe reagent
957:
938:
934:
930:
925:
921:
917:
912:
908:
896:
888:
884:
883:
882:
876:
872:
871:
870:
864:
860:
859:
858:
855:
853:
845:
841:
840:
839:
837:
833:
828:
827:
823:
815:
811:
810:
809:
806:
802:
801:
797:
789:
785:
784:
783:
781:
777:
773:
768:
766:
762:
753:
749:
748:
747:
745:
744:tetrabutyltin
741:
738:
734:
730:
722:
718:
717:
716:
714:
706:
702:
701:
700:
699:(ruled out):
698:
696:
691:
675:
672:
667:
665:
661:
657:
653:
645:
641:
640:
639:
633:
629:
625:
621:
617:
613:
608:
606:
598:
594:
593:
592:
590:
586:
582:
578:
574:
570:
566:
562:
559:
555:
551:
546:
544:
540:
536:
532:
524:
520:
519:
518:
516:
513:
509:
505:
501:
493:
489:
488:
487:
485:
481:
477:
473:
469:
464:
462:
461:nickel effect
458:
454:
450:
440:
438:
434:
429:
427:
423:
419:
415:
411:
410:alpha-olefins
407:
403:
394:
390:
388:
384:
375:
371:
369:
365:
361:
349:
346:
343:
340:
337:
334:
331:
328:
325:
322:
321:
320:
312:
310:
309:nanoparticles
297:
294:Synthesis of
293:
282:
278:
274:
273:1,5-Hexadiene
271:
268:
265:supported on
264:
260:
257:
254:
253:alpha-olefins
250:
247:
244:
240:
239:
238:
236:
222:
218:
216:
212:
208:
199:
195:
193:
189:
185:
181:
177:
173:
161:
157:
149:
145:
135:
133:
129:
125:
121:
117:
113:
109:
105:
101:
97:
93:
89:
85:
76:
67:
63:
59:
56:
53:
52:
48:
44:
41:
40:
35:
31:
28:
27:
22:
19:
6165:Ene reaction
5525:Autoxidation
5386:Degradation
5277:Azo coupling
5054:Ugi reaction
4913:
4654:Ene reaction
4454:Alkynylation
4305:Polyfluorene
4300:Polar effect
4165:Electrophile
4080:Bredt's rule
4050:Baird's rule
4020:Alpha effect
3863:
3837:Applications
3773:Metallocenes
3580:Ene reaction
3510:Halogenation
3484:Ene reaction
3478:
3355:Preparations
3119:
3115:
3094:
3090:
3070:
3066:
3033:(1): 18–29.
3030:
3026:
2989:
2985:
2956:
2952:
2919:
2915:
2895:
2891:
2867:cite journal
2850:
2826:cite journal
2809:
2779:
2775:
2761:
2740:cite journal
2723:
2703:
2690:and Mo(CHCMe
2683:
2675:
2656:
2639:
2635:
2628:
2611:
2607:
2588:
2571:
2567:
2561:
2544:
2540:
2534:
2517:
2513:
2507:
2490:
2486:
2468:
2451:
2447:
2441:
2424:
2420:
2414:
2397:
2393:
2380:
2363:
2359:
2353:
2336:
2332:
2326:
2301:
2297:
2291:
2274:
2270:
2264:
2239:
2235:
2229:
2212:
2208:
2202:
2185:
2181:
2175:
2158:
2154:
2148:
2131:
2127:
2121:
2104:
2100:
2094:
2077:
2073:
2067:
2050:
2046:
2039:
2022:
2018:
2012:
1995:
1991:
1985:
1968:
1964:
1958:
1941:
1937:
1931:
1914:
1910:
1904:
1887:
1883:
1877:
1860:
1856:
1850:
1833:
1829:
1823:
1806:
1802:
1796:
1779:
1775:
1769:
1754:
1737:
1733:
1727:
1702:
1698:
1692:
1675:
1671:
1664:
1647:
1643:
1637:
1625:. Retrieved
1621:the original
1611:
1586:
1582:
1569:
1544:
1540:
1534:
1509:
1505:
1498:
1479:
1473:
1448:
1444:
1423:. Retrieved
1419:the original
1414:
1404:
1387:
1383:
1377:
1359:
1337:(1): 42–56.
1334:
1330:
1324:
1297:
1236:ligand in a
1231:
1219:
1177:
1135:
1108:
1081:complex (PCy
1076:
1035:
1014:
994:
982:
958:
892:
880:
868:
856:
849:
829:
825:
819:
803:
793:
769:
757:
729:cyclopentene
726:
713:metallacycle
710:
693:
689:
674:isotopologue
668:
649:
609:
602:
587:involving a
547:
543:cyclopentene
539:Giulio Natta
528:
515:SNi reaction
497:
479:
465:
446:
430:
399:
380:
357:
318:
306:
232:
229:Applications
204:
170:. A typical
141:
120:Yves Chauvin
104:double bonds
87:
81:
62:RXNO:0000280
57:ontology ID
37:Identifiers
18:
4664:Ethenolysis
4310:Ring strain
4280:Nucleophile
4105:Clar's rule
4045:Aromaticity
3686:spin states
3540:Epoxidation
3091:Tetrahedron
3067:Tetrahedron
2493:: 100–110.
1705:(16): 426.
1148:(replacing
1093:Ru=CHCH=CPh
1061:Ru=CHCH=CPh
832:cyclooctene
589:cyclobutane
414:ethenolysis
348:Ethenolysis
291:on alumina.
281:cyclooctene
108:by-products
7227:Categories
6948:Ozonolysis
6475:Annulation
5825:Ozonolysis
3944:Topics in
3634:Principles
3550:Ozonolysis
3366:haloalkane
2694:R)(N-2,6-C
2666:R)(N-2,6-C
2594:W(O)(CHCMe
2477:(=CHR')(PR
1627:19 January
1278:References
1154:t-butoxide
1028:tolerant.
1001:capnellene
836:molybdenum
776:hybridized
671:deuterated
630:, and the
508:pi complex
472:norbornene
466:In 1960 a
433:ozonolysis
422:norbornene
368:d-orbitals
6462:reactions
5977:reactions
5472:reactions
5388:reactions
5270:reactions
4412:reactions
3885:chemistry
3705:Reactions
3681:Hapticity
3515:Hydration
3498:Reactions
1465:103664623
1425:6 October
1247:polymer.
1245:isotactic
1003:in 1986:
965:isobutene
761:propylene
735:with the
733:2-pentene
697:mechanism
676:yielded C
622:based on
620:2-pentene
573:propylene
558:catalysts
512:concerted
406:propylene
354:Mechanism
259:Neohexene
207:chelating
194:ligands.
138:Catalysts
116:catalysts
4355:Vinylogy
4025:Annulene
3972:Reagents
3146:21160917
3055:22145255
3047:11170353
3006:20000700
2973:19534492
2944:35370749
2936:14533149
2662:Mo(CHCMe
1603:18452296
1561:22731677
1526:20163176
1351:98046245
1251:See also
1191:R){OC(CH
1150:chloride
1122:ethylene
1111:tantalum
1021:tungsten
895:ethylene
822:platinum
664:methanol
660:3-hexene
656:2-butene
581:2-butene
577:ethylene
457:1-butene
453:ethylene
402:ethylene
269:and MgO.
188:alkoxide
154:) using
100:scission
4015:A value
3375:alcohol
3283:Heptene
3249:Pentene
3215:Propene
3191:Alkenes
3184:Alkenes
3137:3002079
3014:4589661
2306:Bibcode
2244:Bibcode
1707:Bibcode
1415:Arkivoc
628:ethanol
614:at the
468:Du Pont
418:styrene
387:entropy
385:, i.e.
344:(ADMET)
176:alumina
166:–EtAlCl
96:alkenes
3384:alkyne
3334:Decene
3317:Nonene
3300:Octene
3266:Hexene
3232:Butene
3198:Ethene
3144:
3134:
3053:
3045:
3012:
3004:
2971:
2942:
2934:
2774:Me)".
2710:)(OCMe
1601:
1559:
1524:
1486:
1463:
1349:
1312:
1160:by an
1156:and a
567:, and
478:using
338:(ROMP)
267:silica
211:ligand
126:, and
90:is an
3382:from
3373:from
3364:from
3051:S2CID
3010:S2CID
2940:S2CID
2770:or CO
2390:(PDF)
1579:(PDF)
1461:S2CID
1347:S2CID
1234:BINOL
1170:(PEt)
1120:with
654:with
556:with
455:into
332:(RCM)
315:Types
192:imido
3142:PMID
3043:PMID
3002:PMID
2969:PMID
2932:PMID
2880:help
2839:help
2753:help
2686:-Bu)
2682:)(O-
2598:(PEt
1676:2007
1629:2012
1599:PMID
1557:PMID
1522:PMID
1484:ISBN
1427:2005
1310:ISBN
1241:ROMP
1195:)(CF
967:and
742:and
731:and
658:and
579:and
482:and
279:and
190:and
110:and
3132:PMC
3124:doi
3099:doi
3075:doi
3035:doi
2994:doi
2990:110
2961:doi
2957:109
2924:doi
2900:doi
2855:doi
2814:doi
2784:doi
2780:115
2728:doi
2724:113
2722:".
2706:-Pr
2678:-Pr
2644:doi
2640:112
2616:doi
2612:102
2606:".
2602:)Cl
2576:doi
2549:doi
2545:101
2522:doi
2495:doi
2491:118
2456:doi
2429:doi
2425:115
2402:doi
2398:114
2368:doi
2364:110
2341:doi
2337:175
2314:doi
2279:doi
2252:doi
2217:doi
2213:108
2190:doi
2186:108
2163:doi
2159:102
2136:doi
2132:100
2109:doi
2082:doi
2055:doi
2027:doi
2000:doi
1973:doi
1946:doi
1919:doi
1892:doi
1888:141
1865:doi
1838:doi
1811:doi
1784:doi
1742:doi
1715:doi
1680:doi
1652:doi
1648:141
1591:doi
1587:130
1549:doi
1514:doi
1453:doi
1392:doi
1339:doi
1302:doi
1152:by
999:of
474:to
463:).
404:or
174:is
158:or
82:In
55:RSC
7229::
3344:20
3340:10
3327:18
3310:16
3293:14
3276:12
3259:10
3140:.
3130:.
3118:.
3114:.
3095:60
3093:.
3071:54
3069:.
3049:.
3041:.
3031:34
3029:.
3008:.
3000:.
2988:.
2967:.
2955:.
2938:.
2930:.
2920:42
2918:.
2896:23
2894:.
2871::
2869:}}
2865:{{
2851:80
2849:.
2830::
2828:}}
2824:{{
2810:80
2808:.
2778:.
2744::
2742:}}
2738:{{
2714:CF
2638:.
2610:.
2570:.
2543:.
2518:96
2516:.
2489:.
2452:34
2450:.
2423:.
2396:.
2392:.
2362:.
2335:.
2312:.
2300:.
2273:.
2250:.
2240:20
2238:.
2211:.
2184:.
2157:.
2130:.
2105:98
2103:.
2078:97
2076:.
2051:96
2049:.
2023:97
2021:.
1996:12
1994:.
1969:94
1967:.
1942:93
1940:.
1915:12
1913:.
1886:.
1861:90
1859:.
1832:.
1805:.
1778:.
1738:82
1736:.
1713:.
1703:67
1701:.
1674:.
1597:.
1585:.
1581:.
1555:.
1545:77
1543:.
1520:.
1510:53
1508:.
1459:.
1449:34
1447:.
1435:^
1413:.
1388:19
1386:.
1345:.
1335:29
1333:.
1308:.
1286:^
1146:Cl
1138:PR
1101:.
1089:Cl
1065::
1057:Cl
1045:,
782:.
746::
666:.
626:,
563:,
537:.
439:.
389:.
217:.
134:.
122:,
118:,
86:,
3937:e
3930:t
3923:v
3619:e
3612:t
3605:v
3347:)
3342:H
3338:C
3336:(
3330:)
3325:H
3323:9
3321:C
3319:(
3313:)
3308:H
3306:8
3304:C
3302:(
3296:)
3291:H
3289:7
3287:C
3285:(
3279:)
3274:H
3272:6
3270:C
3268:(
3262:)
3257:H
3255:5
3253:C
3251:(
3245:)
3242:8
3240:H
3238:4
3236:C
3234:(
3228:)
3225:6
3223:H
3221:3
3219:C
3217:(
3211:)
3208:4
3206:H
3204:2
3202:C
3200:(
3176:e
3169:t
3162:v
3148:.
3126::
3120:6
3105:.
3101::
3081:.
3077::
3057:.
3037::
3016:.
2996::
2975:.
2963::
2946:.
2926::
2906:.
2902::
2882:)
2878:(
2861:.
2857::
2841:)
2837:(
2820:.
2816::
2790:.
2786::
2772:2
2768:3
2755:)
2751:(
2734:.
2730::
2720:2
2718:)
2716:3
2712:2
2708:2
2704:i
2702:-
2700:3
2698:H
2696:6
2692:2
2688:2
2684:t
2680:2
2676:i
2674:-
2672:3
2670:H
2668:6
2664:2
2650:.
2646::
2622:.
2618::
2604:2
2600:3
2596:3
2582:.
2578::
2572:8
2555:.
2551::
2528:.
2524::
2501:.
2497::
2483:2
2481:)
2479:3
2475:2
2462:.
2458::
2435:.
2431::
2408:.
2404::
2374:.
2370::
2347:.
2343::
2320:.
2316::
2308::
2302:3
2285:.
2281::
2275:3
2258:.
2254::
2246::
2223:.
2219::
2196:.
2192::
2169:.
2165::
2142:.
2138::
2115:.
2111::
2088:.
2084::
2061:.
2057::
2033:.
2029::
2006:.
2002::
1979:.
1975::
1952:.
1948::
1925:.
1921::
1898:.
1894::
1871:.
1867::
1844:.
1840::
1834:8
1817:.
1813::
1807:3
1790:.
1786::
1780:3
1748:.
1744::
1721:.
1717::
1709::
1686:.
1682::
1658:.
1654::
1631:.
1605:.
1593::
1563:.
1551::
1528:.
1516::
1492:.
1467:.
1455::
1429:.
1398:.
1394::
1353:.
1341::
1318:.
1304::
1205:2
1203:}
1201:2
1199:)
1197:3
1193:3
1189:2
1187:)
1185:3
1172:3
1168:2
1144:2
1140:3
1117:2
1095:2
1091:2
1087:2
1085:)
1083:3
1063:2
1059:2
1055:2
1053:)
1051:3
944:)
939:0
935:d
931:,
926:2
922:d
918:,
913:4
909:d
905:(
686:4
684:D
682:4
680:H
678:4
636:2
298:,
289:7
287:O
285:2
168:2
164:x
152:x
Text is available under the Creative Commons Attribution-ShareAlike License. Additional terms may apply.
