629:
743:
259:
852:
45:
250:
211:
765:
161:, was performed in an attempt to prove the non-existence of this class of compounds. The situation began to change in the 1950s, and more than 300 papers on allenes have been published in 2012 alone. These compounds are not just interesting intermediates but synthetically valuable targets themselves; for example, over 150 natural products are known with an allene or cumulene fragment.
175:
826:
Many rings or ring systems are known by semisystematic names that assume a maximum number of noncumulative bonds. To unambiguously specify derivatives that include cumulated bonds (and hence fewer hydrogen atoms than would be expected from the skeleton), a lowercase delta may be used with a subscript
339:
Allenes differ considerably from other alkenes in terms of their chemical properties. Compared to isolated and conjugated dienes, they are considerably less stable: comparing the isomeric pentadienes, the allenic 1,2-pentadiene has a heat of formation of 33.6 kcal/mol, compared to 18.1 kcal/mol for
326:
as twisted helical linear combinations of these orthogonal MOs. The symmetry of the system and the degeneracy of these orbitals imply that both descriptions are correct (in the same way that there are infinitely many ways to depict the doubly-degenerate HOMOs and LUMOs of benzene that correspond to
638:
is treated with an organolithium compound (or dissolving metal) and the presumed intermediate rearranges into an allene either directly or via carbene-like species. Notably, even strained allenes can be generated by this procedure. Modifications involving leaving groups of different nature are also
309:
Chiral allenes have been recently used as building blocks in the construction of organic materials with exceptional chiroptical properties. There are a few examples of drug molecule having an allene system in their structure. Mycomycin, an antibiotic with tuberculostatic properties, is a
198:. The bond angle formed by the three carbon atoms is 180°, indicating linear geometry for the central carbon atom. The two terminal carbon atoms are planar, and these planes are twisted 90° from each other. The structure can also be viewed as an "extended tetrahedral" with a similar shape to
354:
The C NMR spectrum of allenes is characterized by the signal of the sp-hybridized carbon atom, resonating at a characteristic 200-220 ppm. In contrast, the sp-hybridized carbon atoms resonate around 80 ppm in a region typical for alkyne and nitrile carbon atoms, while the protons of a
274:
configurations are determined by precedences of the groups attached to the axial section of the molecule when viewed along that axis. The front plane is given higher priority over the other and the final assignment is given from priority 2 to 3 (i.e. the relationship between the two
710:
are located at the 90° angle to each other, and thus require a reagent to approach from somewhat different directions. With an appropriate substitution pattern, allenes exhibit axial chirality as predicted by van’t Hoff as early as 1875. Protonation of allenes gives cations
362:
Allenes possess a rich cycloaddition chemistry, including both and modes of addition, as well as undergoing formal cycloaddition processes catalyzed by transition metals. Allenes also serve as substrates for transition metal catalyzed hydrofunctionalization reactions.
327:
different choices of eigenfunctions in a two-dimensional eigenspace). However, this degeneracy is lifted in substituted allenes, and the helical picture becomes the only symmetry-correct description for the HOMO and HOMO–1 of the C
317:
model describes the bonding of allene using a pair of localized orthogonal π orbitals, the full molecular orbital description of the bonding is more subtle. The symmetry-correct doubly-degenerate HOMOs of allene (adapted to the
217:
The symmetry and isomerism of allenes has long fascinated organic chemists. For allenes with four identical substituents, there exist two twofold axes of rotation through the central carbon atom, inclined at 45° to the
2032:
Lang, Robert W.; Hansen, Hans-Jürgen (1980). "Eine einfache
Allencarbonsäureester-Synthese mittels der Wittig-Reaktion" [A simple synthesis of allene carboxylic acid esters by means of the Wittig reaction].
827:
indicating the number of cumulated double bonds from that atom, e.g. 8δ-benzocyclononene. This may be combined with the λ-convention for specifying nonstandard valency states, e.g. 2λδ,5λδ-thienothiophene.
305:
can be determined by considering the substituents on the front atom followed by the back atom when viewed along the allene axis. For the back atom, only the group of higher priority need be considered.
347:
The C–H bonds of allenes are considerably weaker and more acidic compared to typical vinylic C–H bonds: the bond dissociation energy is 87.7 kcal/mol (compared to 111 kcal/mol in ethylene), while the
513:
157:
For many years, allenes were viewed as curiosities but thought to be synthetically useless and difficult to prepare and to work with. Reportedly, the first synthesis of an allene,
1755:"Inversion of Enantioselectivity in Allene Gas versus Allyl Acetate Reductive Aldehyde Allylation Guided by Metal-Centered Stereogenicity: An Experimental and Computational Study"
3933:
Otsuka, Sei; Nakamura, Akira "Acetylene and allene complexes: their implication in homogeneous catalysis" Advances in
Organometallic Chemistry 1976, volume 14, pp. 245-83.
634:
One of the older methods is the
Skattebøl rearrangement (also called the Doering–Moore–Skattebøl or Doering–LaFlamme rearrangement), in which a gem-dihalocyclopropane
624:
The chemistry of allenes has been reviewed in a number of books and journal articles. Some key approaches towards allenes are outlined in the following scheme:
3795:
Yamano, Michael M.; Kelleghan, Andrew V.; Shao, Qianzhen; Giroud, Maude; Simmons, Bryan J.; Li, Bo; Chen, Shuming; Houk, K. N.; Garg, Neil K. (October 2020).
3738:
Ippoliti, Francesca M.; Adamson, Nathan J.; Wonilowicz, Laura G.; Nasrallah, Daniel J.; Darzi, Evan R.; Donaldson, Joyann S.; Garg, Neil K. (2023-01-20).
726:
and have attracted significant interest in recent years. Numerous cycloadditions are also known, including -, (2+1)-, and -variants, which deliver, e.g.,
1804:"Experimental Studies of Allene, Methylacetylene, and the Propargyl Radical: Bond Dissociation Energies, Gas-Phase Acidities, and Ion-Molecule Chemistry"
875:
3901:
Krause, Norbert; Hoffmann-Röder, Anja (2004). "18. Allenic
Natural Products and Pharmaceuticals". In Krause, Norbert; Hashmi, A. Stephen K. (eds.).
3844:
Westphal, Matthias V.; Hudson, Liam; Mason, Jeremy W.; Pradeilles, Johan A.; Zécri, Frédéric J.; Briner, Karin; Schreiber, Stuart L. (2020-04-29).
351:
is 381 kcal/mol (compared to 409 kcal/mol for ethylene), making it slightly more acidic than the propargylic C–H bond of propyne (382 kcal/mol).
2104:"Allenyllithium Reagents (VI)1. A Highly Regioselective Metalation of Allenic Hydrocarbons2. A Route to Mono, DI, TRI or Tetrasubstituted Allenes"
145:
substituent. While allenes have two consecutive ('cumulated') double bonds, compounds with three or more cumulated double bonds are called
2064:"α-Allenic Esters from α-Phosphoranylidene Esters and Acid Chlorides: Ethyl 2,3-Pentadienoate [2,3-Pentadienoic acid, ethyl ester]"
748:
Another area of allene chemistry involves cyclic allenes, where the allene double bonds exist in a ring. This approach was applied to the
4075:
3951:
Bhagwat, M. M.; Devaprabhakara, D. (1972). "Selective hydrogenation of allenes with chlorotris-(triphenylphosphine) rhodium catalyst".
3081:
Kurtz, Kimberly C.M.; Frederick, Michael O.; Lambeth, Robert H.; Mulder, Jason A.; Tracey, Michael R.; Hsung, Richard P. (April 2006).
4994:
331:-symmetric 1,3-dimethylallene. This qualitative MO description extends to higher odd-carbon cumulenes (e.g., 1,2,3,4-pentatetraene).
298:
5027:
4999:
4031:
3468:
3433:
2971:
2222:
2187:
2152:
1457:
1430:
1103:
552:
795:. Little is known about the biosynthesis, although it is conjectured that they are often generated from alkyne precursors.
285:
because there will no longer be any mirror planes. The chirality of these types of allenes was first predicted in 1875 by
385:
3223:
1843:"Researches on acetylenic compounds. Part XLVII. The prototropic rearrangements of some acetylenic dicarboxylic acids"
1042:"Researches on acetylenic compounds. Part XLVII. The prototropic rearrangements of some acetylenic dicarboxylic acids"
226:. A third twofold axis of rotation passes through the C=C=C bonds, and there is a mirror plane passing through both CH
3918:
571:
540:, which was prepared by Burton and Pechmann in 1887. However, the structure was only correctly identified in 1954.
3846:"Water-Compatible Cycloadditions of Oligonucleotide-Conjugated Strained Allenes for DNA-Encoded Library Synthesis"
4068:
2575:"Gold-Catalyzed Nucleophilic Cyclization of Functionalized Allenes: A Powerful Access to Carbo- and Heterocycles"
286:
310:
typical example. This drug exhibits enantiomerism due to the presence of a suitably substituted allene system.
2477:"Allenes as Three-Carbon Units in Catalytic Cycloadditions: New Opportunities with Transition-Metal Catalysts"
1802:
Robinson, Marin S.; Polak, Mark L.; Bierbaum, Veronica M.; DePuy, Charles H.; Lineberger, W. C. (1995-06-01).
4898:
715:
that undergo further transformations. Reactions with soft electrophiles (e.g. Br) deliver positively charged
141:, a substituent attached to a saturated carbon α (i.e., directly adjacent) to an allene is referred to as an
3582:"Synthesis of ent -Kaurane and Beyerane Diterpenoids by Controlled Fragmentations of Overbred Intermediates"
752:
of lissodendoric acid A. Cyclic allenes also participate in metal-mediated processes. and the generation of
3044:"The ester enolate Claisen rearrangement. Stereochemical control through stereoselective enolate formation"
753:
1093:
856:
195:
2963:
Strategic
Applications of Named Reactions in Organic Synthesis : Background and Detailed Mechanisms
191:
4471:
4061:
4025:
3161:"Base-Catalyzed Endo-Mode Cyclization of Allenes: Easy Preparation of Five- to Nine-Membered Oxacycles"
3083:"Synthesis of chiral allenes from ynamides through a highly stereoselective Saucy–Marbet rearrangement"
359:
group of a terminal allene resonate at around 4.5 ppm — somewhat upfield of a typical vinylic proton.
4048:
1842:
548:
547:
from geminal dihalocyclopropanes and organolithium compounds (or metallic sodium or magnesium) in the
1878:"One-Step Homologation of Acetylenes to Allenes: 4-Hydroxynona-1,2-diene [1,2-Nonadien-4-ol]"
660:
640:
537:
1666:
1274:
H. Hendon, Christopher; Tiana, Davide; T. Murray, Alexander; R. Carbery, David; Walsh, Aron (2013).
4508:
3112:
Mukai, Chisato; Kobayashi, Minoru; Kubota, Shoko; Takahashi, Yukie; Kitagaki, Shinji (March 2004).
799:
3981:"Nomenclature for cyclic organic compounds with contiguous formal double bonds (the δ-convention)"
2876:"The Formation of Allenes from gem-Dihalocyclopropanes by Reaction with Alkyllithium Reagents 1,2"
1482:
4981:
3740:"Total synthesis of lissodendoric acid A via stereospecific trapping of a strained cyclic allene"
3243:
3082:
2277:
Zimmer, Reinhold; Dinesh, Chimmanamada U.; Nandanan, Erathodiyil; Khan, Faiz Ahmed (2000-08-01).
2247:
1539:
815:
612:
from metalation of allene or substituted allenes with BuLi and reaction with electrophiles (RX, R
202:, an analogy that is continued into the stereochemical analysis of certain derivative molecules.
3630:
2995:
Shi, Min; Shao, Li-Xiong; Lu, Jian-Mei; Wei, Yin; Mizuno, Kazuhiko; Maeda, Hajime (2010-10-13).
651:
have been used a number of times to prepare allenic esters and acids. Reactions of vinyl ethers
628:
4881:
1753:
Kim, Seung Wook; Meyer, Cole C.; Mai, Binh Khanh; Liu, Peng; Krische, Michael J. (2019-10-04).
1010:
602:
17:
814:. Ni(0) reagents catalyze the cyclooligomerization of allene. Using a suitable catalyst (e.g.
4988:
4876:
3321:
2833:
Skattebøl, Lars; Nilsson, Martin; Lindberg, Bengt; McKay, James; Munch-Petersen, Jon (1963).
2681:
2476:
963:
691:
Allene itself is the most commonly used member of this family; it exists in equilibrium with
282:
4957:
4402:
1131:
787:
Numerous natural products contain the allene functional group. Noteworthy are the pigments
1712:
Lee, Mitchell; Nguyen, Mary; Brandt, Chance; Kaminsky, Werner; Lalic, Gojko (2017-12-04).
860:
851:
742:
222:
planes at either end of the molecule. The molecule can thus be thought of as a two-bladed
8:
4263:
3953:
907:
The
Chemistry of the Allenes (vol. 1−3); Landor, S. R., Ed.; cademic Press: London, 1982.
585:
314:
31:
3772:
1135:
4002:
3878:
3829:
3700:
3606:
3581:
3523:
2776:
Tejedor, David; Méndez-Abt, Gabriela; Cotos, Leandro; García-Tellado, Fernando (2013).
2457:
1779:
1754:
1642:
1609:
1355:
1322:
1149:
238:
3966:
3938:
3739:
3259:
2263:
1610:"Allenes and Derivatives in Gold(I)- and Platinum(II)-Catalyzed Formal Cycloadditions"
1555:
4947:
4917:
4675:
4297:
3914:
3883:
3865:
3816:
3777:
3759:
3720:
3681:
3646:
3631:"On the stereochemistry of photoaddition between α,β-unsaturated ketones and olefins"
3611:
3562:
3515:
3474:
3464:
3439:
3429:
3391:
3383:
3341:
3302:
3294:
3219:
3188:
3180:
3141:
3133:
3063:
3024:
3016:
2977:
2967:
2942:
2934:
2895:
2856:
2815:
2807:
2753:
2745:
2701:
2654:
2646:
2602:
2594:
2555:
2547:
2523:
2504:
2496:
2461:
2449:
2429:
2410:
2402:
2353:
2345:
2306:
2298:
2228:
2218:
2193:
2183:
2158:
2148:
2123:
2068:
1998:
1974:
1966:
1922:
1882:
1858:
1823:
1784:
1735:
1694:
1686:
1647:
1629:
1590:
1520:
1512:
1463:
1453:
1426:
1360:
1342:
1256:
1247:
Jenkins, D.E. (1950). "Mycomycin: a new antibiotic with tuberculostatic properties".
1229:
1190:
1099:
1057:
991:
983:
941:
655:(the Saucy–Marbet rearrangement) give allene aldehydes, while propargylic sulfenates
567:
64:
56:
4006:
3796:
3527:
3159:
Mukai, Chisato; Ohta, Masaru; Yamashita, Haruhisa; Kitagaki, Shinji (October 2004).
2851:
2834:
885:
5022:
4652:
4146:
4084:
3992:
3962:
3934:
3906:
3873:
3857:
3824:
3808:
3767:
3751:
3712:
3673:
3661:
3642:
3601:
3593:
3554:
3505:
3375:
3333:
3286:
3255:
3211:
3172:
3125:
3094:
3055:
3043:
3008:
2926:
2887:
2875:
2846:
2835:"The Synthesis of Allenes from 1,1-Dihalocyclopropane Derivatives and Alkyllithium"
2797:
2789:
2737:
2693:
2638:
2586:
2539:
2488:
2441:
2392:
2384:
2337:
2290:
2259:
2115:
2077:
2044:
2035:
2007:
1958:
1927:
1891:
1850:
1815:
1774:
1766:
1725:
1678:
1637:
1621:
1582:
1551:
1502:
1494:
1418:
1387:
1350:
1334:
1297:
1287:
1221:
1180:
1153:
1139:
1049:
1022:
975:
933:
921:
889:
880:
3980:
2627:"Allenes from Cyclopropanes and Their Use in Organic SynthesisRecent Developments"
2528:"Transition Metal Catalyzed Cycloisomerizations of 1, n -Allenynes and -Allenenes"
281:
An allene with two different substituents on each of the two carbon atoms will be
4871:
4630:
4625:
4608:
4591:
4392:
4141:
1625:
749:
672:
644:
595:
376:
348:
302:
138:
3845:
3716:
2063:
1993:
1917:
1877:
4942:
4937:
4813:
4808:
4803:
4596:
4563:
4347:
4329:
4319:
3910:
1379:
1338:
1075:
606:
3812:
3098:
2445:
2119:
1570:
258:
5016:
4962:
4910:
4841:
4727:
4717:
4712:
4702:
4697:
4647:
4642:
4558:
4553:
4543:
4397:
4352:
4314:
4302:
4273:
4151:
3869:
3820:
3763:
3724:
3685:
3519:
3478:
3443:
3387:
3363:
3298:
3274:
3215:
3184:
3160:
3137:
3113:
3067:
3020:
2996:
2981:
2938:
2914:
2899:
2860:
2811:
2749:
2705:
2650:
2626:
2598:
2574:
2551:
2527:
2500:
2453:
2406:
2373:"Exploiting [2+2] cycloaddition chemistry: achievements with allenes"
2349:
2325:
2302:
2278:
2232:
2197:
2162:
2127:
2081:
2048:
2011:
1970:
1946:
1931:
1895:
1862:
1827:
1770:
1690:
1633:
1594:
1516:
1483:"Exploiting [2+2] cycloaddition chemistry: achievements with allenes"
1467:
1412:
1346:
1318:
1233:
1061:
1026:
987:
945:
884:, 2nd ed. (the "Gold Book") (1997). Online corrected version: (2006–) "
639:
known. Arguably, the most convenient modern method of allene synthesis is by
158:
91:
3997:
3755:
3510:
3493:
3460:
Synthesis of acetylenes, allenes and cumulenes : methods and techniques
2214:
Synthesis of acetylenes, allenes and cumulenes : methods and techniques
2103:
893:
836:
Compounds with three or more adjacent carbon–carbon double bonds are called
4893:
4780:
4775:
4752:
4503:
4342:
4268:
4205:
4200:
4178:
4134:
4119:
4109:
3887:
3781:
3615:
3597:
3566:
3395:
3345:
3337:
3306:
3192:
3145:
3028:
2946:
2819:
2757:
2677:
2658:
2606:
2559:
2508:
2492:
2414:
2357:
2310:
1978:
1788:
1739:
1730:
1713:
1698:
1651:
1586:
1524:
1449:
Structure determination of organic compounds : tables of spectral data
1364:
1302:
1260:
1194:
1185:
1168:
995:
979:
563:
3458:
3423:
2961:
2915:"Syntheses of gem -Dihalocyclopropanes and Their Use in Organic Synthesis"
2697:
2212:
2177:
2142:
2102:
Michelot, Didier; Clinet, Jean-Claude; Linstrumelle, Gérard (1982-01-01).
1447:
1422:
1323:"Coarctate and Möbius: The Helical Orbitals of Allene and Other Cumulenes"
964:"Synthesis and Properties of Allenic Natural Products and Pharmaceuticals"
4952:
4905:
4866:
4747:
4635:
4620:
4615:
4603:
4168:
4163:
4129:
4124:
4114:
4092:
3861:
3322:"Allenes in Catalytic Asymmetric Synthesis and Natural Product Syntheses"
1854:
1209:
1089:
1053:
1041:
788:
780:
776:
768:
722:. Transition-metal-catalysed reactions proceed via allylic intermediates
375:
is produced industrially on a large scale as an equilibrium mixture with
371:
Although allenes often require specialized syntheses, the parent allene,
234:
134:
72:
3677:
3059:
2891:
2802:
1819:
1225:
937:
4861:
4852:
4732:
4687:
4583:
4548:
4538:
4478:
4414:
4337:
4285:
3797:"Intercepting fleeting cyclic allenes with asymmetric nickel catalysis"
3042:
Ireland, Robert E.; Mueller, Richard H.; Willard, Alvin K. (May 1976).
2793:
2777:
2741:
2725:
2397:
1682:
1507:
1481:
Alcaide, Benito; Almendros, Pedro; Aragoncillo, Cristina (2010-01-28).
1292:
1275:
818:), it is possible to reduce just one of the double bonds of an allene.
647:. Johnson–Claisen and Ireland–Claisen rearrangements of ketene acetals
372:
183:
99:
48:
44:
38:
3379:
3290:
3176:
3129:
3012:
2930:
2642:
2590:
2543:
2341:
2294:
1962:
1803:
4828:
4742:
4707:
4692:
4680:
4523:
4498:
4307:
3558:
3542:
3114:"Construction of Azacycles Based on Endo-Mode Cyclization of Allenes"
2388:
2372:
1498:
1144:
1119:
1011:"Ueber die Einwirkung von Chlorphosphor auf Acetondicarbonsäureäther"
803:
792:
716:
223:
95:
4053:
2775:
1391:
594:
from reaction of a triphenylphosphinyl ester with an acid halide, a
344:)-1,3-pentadiene and 25.4 kcal/mol for the isolated 1,4-pentadiene.
4836:
4790:
4757:
4453:
4359:
4233:
4188:
4173:
1414:
Stereoelectronic
Effects: A Bridge Between Structure and Reactivity
837:
519:
322:
point group) can either be represented by a pair of orthogonal MOs
249:
146:
87:
3737:
2526:; Garcia, Pierre; Malacria, Max; Simonneau, Antoine (2011-03-09).
210:
4798:
4722:
4573:
4568:
4533:
4518:
4513:
4483:
4466:
4290:
4217:
3701:"o -Silylaryl Triflates: A Journey of Kobayashi Aryne Precursors"
3580:
Cherney, Emily C.; Green, Jason C.; Baran, Phil S. (2013-08-19).
2371:
Alcaide, Benito; Almendros, Pedro; Aragoncillo, Cristina (2010).
1608:
Mascareñas, José L.; Varela, Iván; López, Fernando (2019-02-19).
1273:
772:
707:
692:
199:
187:
129:, while a substituent attached to an allene is referred to as an
3364:"Some Typical Advances in the Synthetic Applications of Allenes"
1841:
Jones, E. R. H.; Mansfield, G. H.; Whiting, M. C. (1954-01-01).
1095:
Advanced
Organic Chemistry: Reactions, Mechanisms, and Structure
4886:
4818:
4662:
4371:
4364:
4258:
4239:
4228:
4212:
4158:
2521:
2179:
The chemistry of ketenes, allenes and related compounds. Part 2
2144:
The chemistry of ketenes, allenes and related compounds. Part 1
771:, the most abundant of all carotinoids, is the light-absorbing
703:
The reactivity of substituted allenes has been well explored.
589:
559:
68:
2778:"Propargyl Claisen rearrangement: allene synthesis and beyond"
764:
237:. Because of the symmetry, an unsubstituted allene has no net
4767:
4737:
4670:
4528:
4493:
4488:
4461:
4409:
4376:
4280:
4104:
3843:
3275:"Electrophilic Addition and Cyclization Reactions of Allenes"
3111:
2832:
2326:"Electrophilic Addition and Cyclization Reactions of Allenes"
2182:. PATAI'S Chemistry of Functional Groups. Chichester: Wiley.
2147:. PATAI'S Chemistry of Functional Groups. Chichester: Wiley.
1087:
3543:"Nucleophilic transition metal based cyclization of allenes"
1876:
Crabbé, Pierre; Nassim, Bahman; Robert-Lopes, Maria-Teresa.
1316:
4195:
3080:
2370:
1480:
1452:(Fourth, Revised and Enlarged ed.). Berlin: Springer.
1446:
Pretsch, Ernö; Bühlmann, Philippe; Badertscher, M. (2009).
555:) via rearrangement of cyclopropylidene carbenes/carbenoids
174:
3662:"Synthesis of Some Alkylidenecyclopropanes from Allenes 1"
3541:
Bates, Roderick W.; Satcharoen, Vachiraporn (2002-03-06).
3158:
2101:
1801:
1445:
1276:"Helical frontier orbitals of conjugated linear molecules"
1040:
Jones, E. R. H.; Mansfield, G. H.; Whiting, M. C. (1954).
37:
For the organic compound with the common name allene, see
3794:
3463:. H. D. Verkruijsse (1st ed.). Amsterdam: Elsevier.
3428:(Reference ed.). Hoboken, N.J.: Wiley. p. 526.
543:
Laboratory methods for the formation of allenes include:
482:
429:
400:
2276:
659:
give allene sulfoxides. Allenes can also be prepared by
133:
substituent (R is H or some alkyl group). In analogy to
1711:
1166:
2430:"Allenes as building blocks in heterocyclic chemistry"
1947:"Mechanisms of Nucleophilic Organocopper(I) Reactions"
453:
3950:
3206:
Buckl, Klaus; Meiswinkel, Andreas (2008). "Propyne".
3041:
2475:
López, Fernando; Mascareñas, José Luis (2011-01-10).
1840:
1607:
1039:
388:
3900:
2874:
Moore, William R.; Ward, Harold R. (December 1962).
1875:
1667:"Recent advances in enantioselective gold catalysis"
1120:"Experimental Demonstration of the Allene Asymmetry"
962:
Hoffmann-Röder, Anja; Krause, Norbert (2004-02-27).
961:
526:
of this reaction is –1.9 kcal/mol, corresponding to
508:{\displaystyle {\ce {H2C=C=CH2 <=> H3C-C#CH}}}
230:
planes. Thus this class of molecules belong to the D
3699:Shi, Jiarong; Li, Lianggui; Li, Yang (2021-04-14).
2210:
1167:Rivera Fuentes, Pablo; Diederich, François (2012).
859: by Oleksandr Zhurakovskyi available under the
334:
1945:Yoshikai, Naohiko; Nakamura, Eiichi (2012-04-11).
1008:
507:
289:, but not proven experimentally until 1935. Where
3579:
3494:"Transition-metal-catalyzed reactions of allenes"
3425:Molecular orbitals and organic chemical reactions
2676:
2573:Krause, Norbert; Winter, Christian (2011-03-09).
1569:Alcaide, Benito; Almendros, Pedro (August 2004).
1317:Garner, Marc H.; Hoffmann, Roald; Rettrup, Sten;
461:
460:
443:
442:
5014:
1944:
1916:Luo, Hongwen; Ma, Dengke; Ma, Shengming (2017).
1571:"The Allenic Pauson−Khand Reaction in Synthesis"
1568:
1009:Burton, B. S.; von Pechmann, H. (January 1887).
3540:
3205:
2474:
3208:Ullmann's Encyclopedia of Industrial Chemistry
1752:
1417:. Chichester, UK: John Wiley & Sons, Ltd.
1207:
1098:(6th ed.), New York: Wiley-Interscience,
1015:Berichte der Deutschen Chemischen Gesellschaft
51:, the simplest allene, is also known as allene
4069:
3659:
2966:. Burlington: Elsevier Science. p. 758.
1378:Informatics, NIST Office of Data and (1997).
1117:
522:, is commercially available. At 298 K, the Δ
182:The central carbon atom of allenes forms two
27:Any organic compound containing a C=C=C group
3660:Rahman, W.; Kuivila, Henry G. (March 1966).
2994:
2572:
2427:
75:with each of its two adjacent carbon atoms (
2428:Pinho e Melo, Teresa M. V. D. (July 2011).
1377:
1210:"The Structure of the Antibiotic Mycomycin"
1208:Celmer, Walter D.; Solomons, I. A. (1952).
783:, giving them a brown or olive-green color.
164:
4076:
4062:
2959:
2912:
2279:"Palladium-Catalyzed Reactions of Allenes"
2031:
3996:
3877:
3828:
3771:
3605:
3509:
3320:Yu, Shichao; Ma, Shengming (2012-03-26).
3244:"Recent developments in allene chemistry"
2873:
2850:
2801:
2434:Monatshefte für Chemie - Chemical Monthly
2396:
2248:"Recent developments in allene chemistry"
1847:Journal of the Chemical Society (Resumed)
1778:
1729:
1665:Zi, Weiwei; Toste, F. Dean (2016-08-08).
1641:
1540:"Recent developments in allene chemistry"
1506:
1354:
1301:
1291:
1184:
1143:
1046:Journal of the Chemical Society (Resumed)
671:(nucleophile Nu can be a hydride anion),
3850:Journal of the American Chemical Society
3456:
3048:Journal of the American Chemical Society
2726:"How easy are the syntheses of allenes?"
2682:"Synthesizing Allenes Today (1982-2006)"
2211:Brandsma, L.; Verkruijsse, H.D. (2004).
1991:
1808:Journal of the American Chemical Society
1410:
1214:Journal of the American Chemical Society
763:
194:, and the two terminal carbon atoms are
173:
43:
3698:
3628:
3586:Angewandte Chemie International Edition
3421:
3326:Angewandte Chemie International Edition
1915:
1718:Angewandte Chemie International Edition
1664:
1246:
968:Angewandte Chemie International Edition
536:The first allene to be synthesized was
436:
241:, that is, it is a non-polar molecule.
98:. The parent compound of this class is
14:
5015:
4032:Beilstein Journal of Organic Chemistry
3237:
3235:
2997:"Chemistry of Vinylidenecyclopropanes"
2960:Kurti, Laszlo; Czako, Barbara (2005).
2624:
2062:Lang, Robert W.; Hansen, Hans-Jürgen.
2061:
1714:"Catalytic Hydroalkylation of Allenes"
1118:Maitland, Peter; Mills, W. H. (1935).
919:
4083:
4057:
3357:
3355:
3241:
2771:
2769:
2767:
2719:
2717:
2715:
2672:
2670:
2668:
2620:
2618:
2616:
2245:
2217:(1st ed.). Amsterdam: Elsevier.
2175:
2140:
1575:European Journal of Organic Chemistry
1537:
686:
313:Although the semi-localized textbook
3450:
3319:
2723:
957:
955:
915:
913:
903:
901:
683:, and other, less general, methods.
3266:
3232:
2724:Yu, Shichao; Ma, Shengming (2011).
2204:
821:
756:using cyclic allene intermediates.
581:2′ displacement by an organocuprate
24:
4017:
3491:
3361:
3352:
3272:
2764:
2712:
2665:
2613:
2323:
2317:
2239:
881:Compendium of Chemical Terminology
601:from propargylic alcohols via the
598:accompanied by dehydrohalogenation
558:from reaction of certain terminal
209:
25:
5039:
4042:
3242:Pasto, Daniel J. (January 1984).
2913:Fedoryński, Michał (2003-04-01).
2680:; DeForrest, Jolie (March 2007).
2246:Pasto, Daniel J. (January 1984).
1538:Pasto, Daniel J. (January 1984).
952:
910:
898:
553:Doering–LaFlamme allene synthesis
299:Cahn–Ingold–Prelog priority rules
3666:The Journal of Organic Chemistry
3165:The Journal of Organic Chemistry
3118:The Journal of Organic Chemistry
2880:The Journal of Organic Chemistry
1411:Alabugin, Igor V. (2016-09-19).
1169:"Allenes in Molecular Materials"
855: This article incorporates
850:
741:
627:
335:Chemical and spectral properties
257:
248:
3973:
3944:
3927:
3894:
3837:
3788:
3731:
3692:
3653:
3622:
3573:
3534:
3485:
3415:
3402:
3313:
3199:
3152:
3105:
3074:
3035:
2988:
2953:
2906:
2867:
2852:10.3891/acta.chem.scand.17-1683
2826:
2566:
2515:
2468:
2421:
2364:
2270:
2169:
2134:
2095:
2055:
2025:
1985:
1938:
1909:
1869:
1834:
1795:
1746:
1705:
1658:
1601:
1562:
1531:
1474:
1439:
1404:
1371:
1310:
1267:
1240:
1201:
1160:
920:Taylor, David R. (1967-06-01).
113:), which is itself also called
3412:; P.M. Bazendijk, 1875; p. 43.
2625:Sydnes, Leiv K. (2003-04-01).
2481:Chemistry – A European Journal
1111:
1081:
1068:
1033:
1002:
869:
463:
438:
178:3D view of propadiene (allene)
13:
1:
3967:10.1016/S0040-4039(01)84636-0
3939:10.1016/S0065-3055(08)60654-1
3279:Accounts of Chemical Research
3260:10.1016/S0040-4020(01)91289-X
2330:Accounts of Chemical Research
2264:10.1016/S0040-4020(01)91289-X
1992:Cripps, H. N.; Kiefer, E. F.
1614:Accounts of Chemical Research
1556:10.1016/S0040-4020(01)91289-X
1380:"Welcome to the NIST WebBook"
844:
759:
577:from propargylic halides by S
190:. The central carbon atom is
94:). Allenes are classified as
5028:Jacobus Henricus van 't Hoff
3647:10.1016/0040-4020(75)85082-4
3492:Ma, Shengming (2006-01-01).
3362:Ma, Shengming (2005-07-01).
3273:Ma, Shengming (2009-10-20).
2324:Ma, Shengming (2009-10-20).
1626:10.1021/acs.accounts.8b00567
798:Allenes serve as ligands in
695:as a component of MAPP gas.
366:
293:has a greater priority than
287:Jacobus Henricus van 't Hoff
7:
4023:Brummond, Kay M. (editor).
3717:10.1021/acs.chemrev.0c01011
3629:Wiesner, K. (August 1975).
830:
698:
301:, the configuration of the
205:
169:
117:. A group of the structure
10:
5044:
4029:(special thematic issue).
3911:10.1002/9783527619573.ch18
3498:Pure and Applied Chemistry
2090:, vol. 7, p. 232
1904:, vol. 7, p. 276
1339:10.1021/acscentsci.8b00086
1173:Angew. Chem. Int. Ed. Engl
922:"The Chemistry of Allenes"
802:. A typical complex is Pt(
572:Crabbé–Ma allene synthesis
152:
36:
29:
4971:
4930:
4850:
4827:
4789:
4766:
4661:
4582:
4452:
4429:
4385:
4328:
4251:
4226:
4091:
3813:10.1038/s41586-020-2701-2
3099:10.1016/j.tet.2005.11.087
2839:Acta Chemica Scandinavica
2446:10.1007/s00706-011-0505-7
2176:Patai, Saul, ed. (1980).
2141:Patai, Saul, ed. (1980).
2120:10.1080/00397918208061912
2020:, vol. 5, p. 22
661:nucleophilic substitution
641:sigmatropic rearrangement
538:penta-2,3-dienedioic acid
3547:Chemical Society Reviews
3216:10.1002/14356007.m22_m01
2108:Synthetic Communications
2082:10.15227/orgsyn.062.0202
2049:10.1002/hlca.19800630215
2012:10.15227/orgsyn.042.0012
1932:10.15227/orgsyn.094.0153
1896:10.15227/orgsyn.063.0203
1771:10.1021/acscatal.9b03695
1671:Chemical Society Reviews
1487:Chemical Society Reviews
1027:10.1002/cber.18870200136
800:organometallic chemistry
165:Structure and properties
30:For the given name, see
4982:chemical classification
3998:10.1351/pac198860091395
3903:Modern Allene Chemistry
3756:10.1126/science.ade0032
3511:10.1351/pac200678020197
3410:La Chimie dans l’Espace
2730:Chemical Communications
894:10.1351/goldbook.A00238
549:Skattebøl rearrangement
518:This mixture, known as
3598:10.1002/anie.201304609
3338:10.1002/anie.201101460
2493:10.1002/chem.201002366
1731:10.1002/anie.201709144
1587:10.1002/ejoc.200400023
1186:10.1002/anie.201108001
980:10.1002/anie.200300628
784:
645:propargylic substrates
603:Myers allene synthesis
509:
214:
179:
52:
4989:chemical nomenclature
3905:. pp. 997–1040.
3457:Brandsma, L. (2004).
3422:Fleming, Ian (2010).
2698:10.1055/s-2007-965963
1423:10.1002/9781118906378
767:
754:DNA-encoded libraries
679:, proton transfer in
510:
213:
177:
47:
4049:Synthesis of allenes
3862:10.1021/jacs.9b13186
1918:"Buta-2,3-dien-1-ol"
1855:10.1039/JR9540003208
1054:10.1039/jr9540003208
816:Wilkinson's catalyst
386:
4445:not C, H or O)
3991:: 1395-1401. 1988.
3954:Tetrahedron Letters
3678:10.1021/jo01341a029
3408:Van ’t Hoff, J. H.
3060:10.1021/ja00426a033
2892:10.1021/jo01059a013
1820:10.1021/ja00130a017
1724:(49): 15703–15707.
1327:ACS Central Science
1226:10.1021/ja01127a529
1136:1935Natur.135Q.994M
1088:Smith, Michael B.;
938:10.1021/cr60247a004
586:dehydrohalogenation
484:
449:
431:
402:
32:Allene (given name)
4887:Hypervalent iodine
2794:10.1039/C2CS35311C
2742:10.1039/C0CC05640E
2524:Fensterbank, Louis
1683:10.1039/C5CS00929D
1293:10.1039/C3SC52061G
785:
687:Use and occurrence
570:, and added base (
505:
472:
468:
419:
390:
215:
180:
53:
5010:
5009:
4948:Sulfenyl chloride
4926:
4925:
4425:
4424:
4244:(only C, H and O)
4085:Functional groups
3961:(15): 1391–1392.
3856:(17): 7776–7782.
3807:(7828): 242–247.
3750:(6629): 261–265.
3641:(15): 1655–1658.
3592:(34): 9019–9022.
3470:978-0-12-125751-4
3435:978-0-470-68949-3
3380:10.1021/cr020024j
3332:(13): 3074–3112.
3291:10.1021/ar900153r
3285:(10): 1679–1688.
3254:(15): 2805–2827.
3177:10.1021/jo0488614
3171:(20): 6867–6873.
3130:10.1021/jo035729f
3093:(16): 3928–3938.
3054:(10): 2868–2877.
3013:10.1021/cr900381k
3007:(10): 5883–5913.
2973:978-0-08-057541-4
2931:10.1021/cr0100087
2886:(12): 4179–4181.
2736:(19): 5384–5418.
2643:10.1021/cr010025w
2591:10.1021/cr1004088
2544:10.1021/cr100376w
2522:Aubert, Corinne;
2342:10.1021/ar900153r
2336:(10): 1679–1688.
2295:10.1021/cr9902796
2258:(15): 2805–2827.
2224:978-0-12-125751-4
2189:978-0-470-77161-7
2154:978-0-470-77160-0
2088:Collected Volumes
2069:Organic Syntheses
2018:Collected Volumes
1999:Organic Syntheses
1963:10.1021/cr200241f
1923:Organic Syntheses
1902:Collected Volumes
1883:Organic Syntheses
1814:(25): 6766–6778.
1765:(10): 9158–9163.
1677:(16): 4567–4589.
1581:(16): 3377–3383.
1550:(15): 2805–2827.
1459:978-3-540-93810-1
1432:978-1-118-90637-8
1319:Solomon, Gemma C.
1286:(11): 4278–4284.
1179:(12): 2818–2828.
1105:978-0-471-72091-1
974:(10): 1196–1216.
568:copper(I) bromide
503:
495:
487:
475:
470:
422:
413:
405:
393:
349:gas-phase acidity
297:according to the
65:organic compounds
57:organic chemistry
16:(Redirected from
5035:
4977:
4882:Trifluoromethoxy
4450:
4449:
4446:
4249:
4248:
4245:
4098:
4078:
4071:
4064:
4055:
4054:
4026:Allene chemistry
4011:
4010:
4000:
3977:
3971:
3970:
3948:
3942:
3931:
3925:
3924:
3898:
3892:
3891:
3881:
3841:
3835:
3834:
3832:
3792:
3786:
3785:
3775:
3735:
3729:
3728:
3711:(7): 3892–4044.
3705:Chemical Reviews
3696:
3690:
3689:
3657:
3651:
3650:
3626:
3620:
3619:
3609:
3577:
3571:
3570:
3559:10.1039/b103904k
3538:
3532:
3531:
3513:
3489:
3483:
3482:
3454:
3448:
3447:
3419:
3413:
3406:
3400:
3399:
3374:(7): 2829–2872.
3368:Chemical Reviews
3359:
3350:
3349:
3317:
3311:
3310:
3270:
3264:
3263:
3239:
3230:
3229:
3203:
3197:
3196:
3156:
3150:
3149:
3124:(6): 2128–2136.
3109:
3103:
3102:
3078:
3072:
3071:
3039:
3033:
3032:
3001:Chemical Reviews
2992:
2986:
2985:
2957:
2951:
2950:
2925:(4): 1099–1132.
2919:Chemical Reviews
2910:
2904:
2903:
2871:
2865:
2864:
2854:
2830:
2824:
2823:
2805:
2773:
2762:
2761:
2721:
2710:
2709:
2674:
2663:
2662:
2637:(4): 1133–1150.
2631:Chemical Reviews
2622:
2611:
2610:
2585:(3): 1994–2009.
2579:Chemical Reviews
2570:
2564:
2563:
2538:(3): 1954–1993.
2532:Chemical Reviews
2519:
2513:
2512:
2472:
2466:
2465:
2425:
2419:
2418:
2400:
2389:10.1039/B913749A
2368:
2362:
2361:
2321:
2315:
2314:
2289:(8): 3067–3126.
2283:Chemical Reviews
2274:
2268:
2267:
2243:
2237:
2236:
2208:
2202:
2201:
2173:
2167:
2166:
2138:
2132:
2131:
2099:
2093:
2091:
2084:
2059:
2053:
2052:
2036:Helv. Chim. Acta
2029:
2023:
2021:
2014:
1989:
1983:
1982:
1957:(4): 2339–2372.
1951:Chemical Reviews
1942:
1936:
1934:
1913:
1907:
1905:
1898:
1873:
1867:
1866:
1838:
1832:
1831:
1799:
1793:
1792:
1782:
1750:
1744:
1743:
1733:
1709:
1703:
1702:
1662:
1656:
1655:
1645:
1605:
1599:
1598:
1566:
1560:
1559:
1535:
1529:
1528:
1510:
1499:10.1039/B913749A
1478:
1472:
1471:
1443:
1437:
1436:
1408:
1402:
1401:
1399:
1398:
1384:webbook.nist.gov
1375:
1369:
1368:
1358:
1314:
1308:
1307:
1305:
1295:
1280:Chemical Science
1271:
1265:
1264:
1244:
1238:
1237:
1220:(7): 1870–1871.
1205:
1199:
1198:
1188:
1164:
1158:
1157:
1147:
1145:10.1038/135994a0
1115:
1109:
1108:
1085:
1079:
1072:
1066:
1065:
1037:
1031:
1030:
1006:
1000:
999:
959:
950:
949:
926:Chemical Reviews
917:
908:
905:
896:
873:
854:
822:Delta convention
745:
738:, respectively.
631:
514:
512:
511:
506:
504:
501:
500:
493:
492:
485:
483:
480:
473:
471:
469:
467:
466:
459:
451:
450:
448:
441:
433:
430:
427:
420:
418:
411:
410:
403:
401:
398:
391:
261:
252:
124:
112:
96:cumulated dienes
85:
21:
5043:
5042:
5038:
5037:
5036:
5034:
5033:
5032:
5013:
5012:
5011:
5006:
4975:
4967:
4922:
4877:Trichloromethyl
4872:Trifluoromethyl
4846:
4823:
4785:
4762:
4657:
4626:Phosphine oxide
4578:
4444:
4442:
4441:
4439:
4437:
4435:
4433:
4431:
4421:
4381:
4324:
4243:
4242:
4237:
4232:
4222:
4096:
4095:
4087:
4082:
4045:
4020:
4018:Further reading
4015:
4014:
3985:Pure Appl. Chem
3979:
3978:
3974:
3949:
3945:
3932:
3928:
3921:
3899:
3895:
3842:
3838:
3793:
3789:
3736:
3732:
3697:
3693:
3658:
3654:
3627:
3623:
3578:
3574:
3539:
3535:
3490:
3486:
3471:
3455:
3451:
3436:
3420:
3416:
3407:
3403:
3360:
3353:
3318:
3314:
3271:
3267:
3240:
3233:
3226:
3204:
3200:
3157:
3153:
3110:
3106:
3079:
3075:
3040:
3036:
2993:
2989:
2974:
2958:
2954:
2911:
2907:
2872:
2868:
2831:
2827:
2774:
2765:
2722:
2713:
2675:
2666:
2623:
2614:
2571:
2567:
2520:
2516:
2473:
2469:
2426:
2422:
2369:
2365:
2322:
2318:
2275:
2271:
2244:
2240:
2225:
2209:
2205:
2190:
2174:
2170:
2155:
2139:
2135:
2114:(10): 739–747.
2100:
2096:
2086:
2060:
2056:
2030:
2026:
2016:
1990:
1986:
1943:
1939:
1914:
1910:
1900:
1874:
1870:
1839:
1835:
1800:
1796:
1751:
1747:
1710:
1706:
1663:
1659:
1606:
1602:
1567:
1563:
1536:
1532:
1479:
1475:
1460:
1444:
1440:
1433:
1409:
1405:
1396:
1394:
1392:10.18434/T4D303
1376:
1372:
1315:
1311:
1272:
1268:
1245:
1241:
1206:
1202:
1165:
1161:
1116:
1112:
1106:
1086:
1082:
1073:
1069:
1038:
1034:
1007:
1003:
960:
953:
918:
911:
906:
899:
874:
870:
847:
833:
824:
813:
809:
762:
750:total synthesis
701:
689:
673:1,2-elimination
619:
615:
596:Wittig reaction
580:
532:
496:
488:
481:
476:
462:
455:
454:
452:
444:
437:
435:
434:
432:
428:
423:
414:
406:
399:
394:
389:
387:
384:
383:
369:
358:
337:
330:
321:
303:axial chirality
279:
278:
277:
276:
264:
263:
262:
254:
253:
233:
229:
221:
208:
172:
167:
155:
122:
118:
111:
107:
103:
84:
80:
76:
42:
35:
28:
23:
22:
15:
12:
11:
5:
5041:
5031:
5030:
5025:
5008:
5007:
5005:
5004:
5003:
5002:
4997:
4985:
4978:
4972:
4969:
4968:
4966:
4965:
4963:Sulfinylamines
4960:
4955:
4950:
4945:
4943:Phosphoramides
4940:
4938:Isothiocyanate
4934:
4932:
4928:
4927:
4924:
4923:
4921:
4920:
4915:
4914:
4913:
4903:
4902:
4901:
4891:
4890:
4889:
4884:
4879:
4874:
4869:
4858:
4856:
4848:
4847:
4845:
4844:
4839:
4833:
4831:
4825:
4824:
4822:
4821:
4816:
4814:Selenenic acid
4811:
4809:Seleninic acid
4806:
4804:Selenonic acid
4801:
4795:
4793:
4787:
4786:
4784:
4783:
4778:
4772:
4770:
4764:
4763:
4761:
4760:
4755:
4750:
4745:
4740:
4735:
4730:
4725:
4720:
4715:
4710:
4705:
4700:
4695:
4690:
4685:
4684:
4683:
4673:
4667:
4665:
4659:
4658:
4656:
4655:
4650:
4645:
4640:
4639:
4638:
4628:
4623:
4618:
4613:
4612:
4611:
4601:
4600:
4599:
4597:Phosphodiester
4588:
4586:
4580:
4579:
4577:
4576:
4571:
4566:
4561:
4556:
4551:
4546:
4541:
4536:
4531:
4526:
4521:
4516:
4511:
4506:
4501:
4496:
4491:
4486:
4481:
4476:
4475:
4474:
4469:
4458:
4456:
4447:
4443:(one element,
4427:
4426:
4423:
4422:
4420:
4419:
4418:
4417:
4407:
4406:
4405:
4400:
4389:
4387:
4383:
4382:
4380:
4379:
4374:
4369:
4368:
4367:
4357:
4356:
4355:
4350:
4345:
4334:
4332:
4326:
4325:
4323:
4322:
4320:Methylenedioxy
4317:
4312:
4311:
4310:
4305:
4295:
4294:
4293:
4288:
4278:
4277:
4276:
4266:
4261:
4255:
4253:
4246:
4224:
4223:
4221:
4220:
4215:
4210:
4209:
4208:
4203:
4193:
4192:
4191:
4186:
4181:
4176:
4171:
4166:
4156:
4155:
4154:
4149:
4139:
4138:
4137:
4132:
4127:
4122:
4117:
4112:
4101:
4099:
4097:(only C and H)
4089:
4088:
4081:
4080:
4073:
4066:
4058:
4052:
4051:
4044:
4043:External links
4041:
4040:
4039:
4019:
4016:
4013:
4012:
3972:
3943:
3926:
3919:
3893:
3836:
3787:
3730:
3691:
3672:(3): 772–776.
3652:
3621:
3572:
3533:
3504:(2): 197–208.
3484:
3469:
3449:
3434:
3414:
3401:
3351:
3312:
3265:
3231:
3225:978-3527306732
3224:
3198:
3151:
3104:
3073:
3034:
2987:
2972:
2952:
2905:
2866:
2825:
2788:(2): 458–471.
2782:Chem. Soc. Rev
2763:
2711:
2692:(6): 795–818.
2664:
2612:
2565:
2514:
2487:(2): 418–428.
2467:
2440:(7): 681–697.
2420:
2383:(2): 783–816.
2377:Chem. Soc. Rev
2363:
2316:
2269:
2238:
2223:
2203:
2188:
2168:
2153:
2133:
2094:
2054:
2043:(2): 438–455.
2024:
1984:
1937:
1908:
1868:
1833:
1794:
1745:
1704:
1657:
1620:(2): 465–479.
1600:
1561:
1530:
1493:(2): 783–816.
1473:
1458:
1438:
1431:
1403:
1370:
1333:(6): 688–700.
1321:(2018-06-27).
1309:
1266:
1249:J Lab Clin Med
1239:
1200:
1159:
1110:
1104:
1080:
1076:Web of Science
1074:Data from the
1067:
1032:
1021:(1): 145–149.
1001:
951:
932:(3): 317–359.
909:
897:
867:
866:
846:
843:
842:
841:
832:
829:
823:
820:
811:
807:
761:
758:
700:
697:
688:
685:
622:
621:
617:
613:
610:
607:stereospecific
599:
592:
582:
578:
575:
556:
530:
516:
515:
499:
491:
479:
465:
458:
447:
440:
426:
417:
409:
397:
368:
365:
356:
336:
333:
328:
319:
315:σ-π separation
266:
265:
256:
255:
247:
246:
245:
244:
243:
231:
227:
219:
207:
204:
171:
168:
166:
163:
154:
151:
120:
109:
105:
82:
78:
26:
9:
6:
4:
3:
2:
5040:
5029:
5026:
5024:
5021:
5020:
5018:
5001:
4998:
4996:
4993:
4992:
4991:
4990:
4986:
4984:
4983:
4979:
4974:
4973:
4970:
4964:
4961:
4959:
4956:
4954:
4951:
4949:
4946:
4944:
4941:
4939:
4936:
4935:
4933:
4929:
4919:
4916:
4912:
4909:
4908:
4907:
4904:
4900:
4897:
4896:
4895:
4892:
4888:
4885:
4883:
4880:
4878:
4875:
4873:
4870:
4868:
4865:
4864:
4863:
4860:
4859:
4857:
4855:
4854:
4849:
4843:
4842:Telluroketone
4840:
4838:
4835:
4834:
4832:
4830:
4826:
4820:
4817:
4815:
4812:
4810:
4807:
4805:
4802:
4800:
4797:
4796:
4794:
4792:
4788:
4782:
4779:
4777:
4774:
4773:
4771:
4769:
4765:
4759:
4756:
4754:
4751:
4749:
4746:
4744:
4741:
4739:
4736:
4734:
4731:
4729:
4728:Sulfonic acid
4726:
4724:
4721:
4719:
4718:Sulfinic acid
4716:
4714:
4713:Thiosulfonate
4711:
4709:
4706:
4704:
4703:Thiosulfinate
4701:
4699:
4698:Sulfenic acid
4696:
4694:
4691:
4689:
4686:
4682:
4679:
4678:
4677:
4674:
4672:
4669:
4668:
4666:
4664:
4660:
4654:
4653:Phosphaallene
4651:
4649:
4648:Phosphaalkyne
4646:
4644:
4643:Phosphaalkene
4641:
4637:
4634:
4633:
4632:
4629:
4627:
4624:
4622:
4619:
4617:
4614:
4610:
4607:
4606:
4605:
4602:
4598:
4595:
4594:
4593:
4590:
4589:
4587:
4585:
4581:
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:
4473:
4470:
4468:
4465:
4464:
4463:
4460:
4459:
4457:
4455:
4451:
4448:
4428:
4416:
4413:
4412:
4411:
4408:
4404:
4401:
4399:
4396:
4395:
4394:
4391:
4390:
4388:
4384:
4378:
4375:
4373:
4370:
4366:
4363:
4362:
4361:
4358:
4354:
4351:
4349:
4346:
4344:
4341:
4340:
4339:
4336:
4335:
4333:
4331:
4327:
4321:
4318:
4316:
4315:Ethylenedioxy
4313:
4309:
4306:
4304:
4301:
4300:
4299:
4296:
4292:
4289:
4287:
4284:
4283:
4282:
4279:
4275:
4272:
4271:
4270:
4267:
4265:
4262:
4260:
4257:
4256:
4254:
4250:
4247:
4241:
4235:
4230:
4225:
4219:
4216:
4214:
4211:
4207:
4204:
4202:
4199:
4198:
4197:
4194:
4190:
4187:
4185:
4182:
4180:
4177:
4175:
4172:
4170:
4167:
4165:
4162:
4161:
4160:
4157:
4153:
4150:
4148:
4145:
4144:
4143:
4140:
4136:
4133:
4131:
4128:
4126:
4123:
4121:
4118:
4116:
4113:
4111:
4108:
4107:
4106:
4103:
4102:
4100:
4094:
4090:
4086:
4079:
4074:
4072:
4067:
4065:
4060:
4059:
4056:
4050:
4047:
4046:
4037:
4034:
4033:
4028:
4027:
4022:
4021:
4008:
4004:
3999:
3994:
3990:
3986:
3982:
3976:
3968:
3964:
3960:
3956:
3955:
3947:
3940:
3936:
3930:
3922:
3920:9783527619573
3916:
3912:
3908:
3904:
3897:
3889:
3885:
3880:
3875:
3871:
3867:
3863:
3859:
3855:
3851:
3847:
3840:
3831:
3826:
3822:
3818:
3814:
3810:
3806:
3802:
3798:
3791:
3783:
3779:
3774:
3769:
3765:
3761:
3757:
3753:
3749:
3745:
3741:
3734:
3726:
3722:
3718:
3714:
3710:
3706:
3702:
3695:
3687:
3683:
3679:
3675:
3671:
3667:
3663:
3656:
3648:
3644:
3640:
3636:
3632:
3625:
3617:
3613:
3608:
3603:
3599:
3595:
3591:
3587:
3583:
3576:
3568:
3564:
3560:
3556:
3552:
3548:
3544:
3537:
3529:
3525:
3521:
3517:
3512:
3507:
3503:
3499:
3495:
3488:
3480:
3476:
3472:
3466:
3462:
3461:
3453:
3445:
3441:
3437:
3431:
3427:
3426:
3418:
3411:
3405:
3397:
3393:
3389:
3385:
3381:
3377:
3373:
3369:
3365:
3358:
3356:
3347:
3343:
3339:
3335:
3331:
3327:
3323:
3316:
3308:
3304:
3300:
3296:
3292:
3288:
3284:
3280:
3276:
3269:
3261:
3257:
3253:
3249:
3245:
3238:
3236:
3227:
3221:
3217:
3213:
3209:
3202:
3194:
3190:
3186:
3182:
3178:
3174:
3170:
3166:
3162:
3155:
3147:
3143:
3139:
3135:
3131:
3127:
3123:
3119:
3115:
3108:
3100:
3096:
3092:
3088:
3084:
3077:
3069:
3065:
3061:
3057:
3053:
3049:
3045:
3038:
3030:
3026:
3022:
3018:
3014:
3010:
3006:
3002:
2998:
2991:
2983:
2979:
2975:
2969:
2965:
2964:
2956:
2948:
2944:
2940:
2936:
2932:
2928:
2924:
2920:
2916:
2909:
2901:
2897:
2893:
2889:
2885:
2881:
2877:
2870:
2862:
2858:
2853:
2848:
2845:: 1683–1693.
2844:
2840:
2836:
2829:
2821:
2817:
2813:
2809:
2804:
2799:
2795:
2791:
2787:
2783:
2779:
2772:
2770:
2768:
2759:
2755:
2751:
2747:
2743:
2739:
2735:
2731:
2727:
2720:
2718:
2716:
2707:
2703:
2699:
2695:
2691:
2687:
2683:
2679:
2678:Brummond, Kay
2673:
2671:
2669:
2660:
2656:
2652:
2648:
2644:
2640:
2636:
2632:
2628:
2621:
2619:
2617:
2608:
2604:
2600:
2596:
2592:
2588:
2584:
2580:
2576:
2569:
2561:
2557:
2553:
2549:
2545:
2541:
2537:
2533:
2529:
2525:
2518:
2510:
2506:
2502:
2498:
2494:
2490:
2486:
2482:
2478:
2471:
2463:
2459:
2455:
2451:
2447:
2443:
2439:
2435:
2431:
2424:
2416:
2412:
2408:
2404:
2399:
2394:
2390:
2386:
2382:
2378:
2374:
2367:
2359:
2355:
2351:
2347:
2343:
2339:
2335:
2331:
2327:
2320:
2312:
2308:
2304:
2300:
2296:
2292:
2288:
2284:
2280:
2273:
2265:
2261:
2257:
2253:
2249:
2242:
2234:
2230:
2226:
2220:
2216:
2215:
2207:
2199:
2195:
2191:
2185:
2181:
2180:
2172:
2164:
2160:
2156:
2150:
2146:
2145:
2137:
2129:
2125:
2121:
2117:
2113:
2109:
2105:
2098:
2089:
2083:
2079:
2075:
2071:
2070:
2065:
2058:
2050:
2046:
2042:
2038:
2037:
2028:
2019:
2013:
2009:
2005:
2001:
2000:
1995:
1988:
1980:
1976:
1972:
1968:
1964:
1960:
1956:
1952:
1948:
1941:
1933:
1929:
1925:
1924:
1919:
1912:
1903:
1897:
1893:
1889:
1885:
1884:
1879:
1872:
1864:
1860:
1856:
1852:
1849:: 3208–3212.
1848:
1844:
1837:
1829:
1825:
1821:
1817:
1813:
1809:
1805:
1798:
1790:
1786:
1781:
1776:
1772:
1768:
1764:
1760:
1759:ACS Catalysis
1756:
1749:
1741:
1737:
1732:
1727:
1723:
1719:
1715:
1708:
1700:
1696:
1692:
1688:
1684:
1680:
1676:
1672:
1668:
1661:
1653:
1649:
1644:
1639:
1635:
1631:
1627:
1623:
1619:
1615:
1611:
1604:
1596:
1592:
1588:
1584:
1580:
1576:
1572:
1565:
1557:
1553:
1549:
1545:
1541:
1534:
1526:
1522:
1518:
1514:
1509:
1504:
1500:
1496:
1492:
1488:
1484:
1477:
1469:
1465:
1461:
1455:
1451:
1450:
1442:
1434:
1428:
1424:
1420:
1416:
1415:
1407:
1393:
1389:
1385:
1381:
1374:
1366:
1362:
1357:
1352:
1348:
1344:
1340:
1336:
1332:
1328:
1324:
1320:
1313:
1304:
1303:10044/1/41564
1299:
1294:
1289:
1285:
1281:
1277:
1270:
1262:
1258:
1254:
1250:
1243:
1235:
1231:
1227:
1223:
1219:
1215:
1211:
1204:
1196:
1192:
1187:
1182:
1178:
1174:
1170:
1163:
1155:
1151:
1146:
1141:
1137:
1133:
1130:(3424): 994.
1129:
1125:
1121:
1114:
1107:
1101:
1097:
1096:
1091:
1084:
1077:
1071:
1063:
1059:
1055:
1051:
1048:: 3208–3212.
1047:
1043:
1036:
1028:
1024:
1020:
1017:(in German).
1016:
1012:
1005:
997:
993:
989:
985:
981:
977:
973:
969:
965:
958:
956:
947:
943:
939:
935:
931:
927:
923:
916:
914:
904:
902:
895:
891:
887:
883:
882:
877:
872:
868:
865:
864:
862:
858:
853:
839:
835:
834:
828:
819:
817:
805:
801:
796:
794:
790:
782:
778:
774:
770:
766:
757:
755:
751:
746:
744:
739:
737:
733:
729:
725:
721:
718:
714:
709:
704:
696:
694:
684:
682:
678:
674:
670:
666:
662:
658:
654:
650:
646:
642:
637:
632:
630:
625:
611:
608:
604:
600:
597:
593:
591:
587:
583:
576:
573:
569:
565:
561:
557:
554:
550:
546:
545:
544:
541:
539:
534:
529:
525:
521:
497:
489:
477:
456:
445:
424:
415:
407:
395:
382:
381:
380:
378:
374:
364:
360:
352:
350:
345:
343:
332:
325:
316:
311:
307:
304:
300:
296:
292:
288:
284:
273:
269:
260:
251:
242:
240:
239:dipole moment
236:
225:
212:
203:
201:
197:
196:sp-hybridized
193:
192:sp-hybridized
189:
185:
176:
162:
160:
159:glutinic acid
150:
148:
144:
140:
136:
132:
128:
116:
101:
97:
93:
92:organyl group
89:
86:, where R is
74:
70:
67:in which one
66:
62:
58:
50:
46:
40:
33:
19:
4987:
4980:
4894:Vinyl halide
4851:
4781:Borinic acid
4776:Boronic acid
4753:Thioxanthate
4183:
4093:Hydrocarbons
4035:
4030:
4024:
3988:
3984:
3975:
3958:
3952:
3946:
3929:
3902:
3896:
3853:
3849:
3839:
3804:
3800:
3790:
3747:
3743:
3733:
3708:
3704:
3694:
3669:
3665:
3655:
3638:
3634:
3624:
3589:
3585:
3575:
3553:(1): 12–21.
3550:
3546:
3536:
3501:
3497:
3487:
3459:
3452:
3424:
3417:
3409:
3404:
3371:
3367:
3329:
3325:
3315:
3282:
3278:
3268:
3251:
3247:
3207:
3201:
3168:
3164:
3154:
3121:
3117:
3107:
3090:
3086:
3076:
3051:
3047:
3037:
3004:
3000:
2990:
2962:
2955:
2922:
2918:
2908:
2883:
2879:
2869:
2842:
2838:
2828:
2803:10261/132538
2785:
2781:
2733:
2729:
2689:
2685:
2634:
2630:
2582:
2578:
2568:
2535:
2531:
2517:
2484:
2480:
2470:
2437:
2433:
2423:
2380:
2376:
2366:
2333:
2329:
2319:
2286:
2282:
2272:
2255:
2251:
2241:
2213:
2206:
2178:
2171:
2143:
2136:
2111:
2107:
2097:
2087:
2073:
2067:
2057:
2040:
2034:
2027:
2017:
2003:
1997:
1987:
1954:
1950:
1940:
1921:
1911:
1901:
1887:
1881:
1871:
1846:
1836:
1811:
1807:
1797:
1762:
1758:
1748:
1721:
1717:
1707:
1674:
1670:
1660:
1617:
1613:
1603:
1578:
1574:
1564:
1547:
1543:
1533:
1490:
1486:
1476:
1448:
1441:
1413:
1406:
1395:. Retrieved
1383:
1373:
1330:
1326:
1312:
1283:
1279:
1269:
1255:(5): 841–2.
1252:
1248:
1242:
1217:
1213:
1203:
1176:
1172:
1162:
1127:
1123:
1113:
1094:
1090:March, Jerry
1083:
1070:
1045:
1035:
1018:
1014:
1004:
971:
967:
929:
925:
879:
871:
849:
848:
825:
806:-allene)(PPh
797:
786:
777:chloroplasts
747:
740:
735:
731:
727:
723:
719:
712:
705:
702:
690:
680:
676:
668:
664:
656:
652:
648:
635:
633:
626:
623:
564:formaldehyde
542:
535:
527:
523:
517:
370:
361:
353:
346:
341:
338:
323:
312:
308:
294:
290:
280:
271:
267:
216:
181:
156:
142:
130:
126:
114:
73:double bonds
60:
54:
4958:Thiocyanate
4953:Sulfonamide
4918:Perchlorate
4906:Acyl halide
4867:Fluoroethyl
4748:Thionoester
4636:Phosphonium
4621:Phosphinate
4616:Phosphonous
4604:Phosphonate
4303:Hydroperoxy
4125:Cyclopropyl
3635:Tetrahedron
3248:Tetrahedron
3087:Tetrahedron
2398:10261/29537
2252:Tetrahedron
1926:: 153–166.
1544:Tetrahedron
1508:10261/29537
789:fucoxanthin
781:brown algae
769:Fucoxanthin
605:protocol—a
588:of certain
235:point group
184:sigma bonds
139:propargylic
5017:Categories
4862:Haloalkane
4733:Thioketone
4688:Persulfide
4584:Phosphorus
4549:Isocyanate
4539:Isonitrile
4440:or oxygen
4438:hydrogen,
4434:not being
4415:Orthoester
4308:Dioxiranes
4286:Enol ether
4174:1-Propenyl
4038:: 394–943.
1397:2020-10-17
845:References
760:Occurrence
717:onium ions
373:propadiene
125:is called
100:propadiene
49:Propadiene
39:Propadiene
4995:inorganic
4829:Tellurium
4743:Thioester
4708:Sulfoxide
4693:Disulfide
4681:Sulfonium
4631:Phosphine
4609:Phosphite
4592:Phosphate
4524:Carbamate
4499:Hydrazone
4432:element,
4430:Only one
4403:Anhydride
4142:Methylene
3870:0002-7863
3821:1476-4687
3764:0036-8075
3725:0009-2665
3686:0022-3263
3520:1365-3075
3479:162570992
3444:607520014
3388:0009-2665
3299:0001-4842
3185:0022-3263
3138:0022-3263
3068:0002-7863
3021:0009-2665
2982:850164343
2939:0009-2665
2900:0022-3263
2861:0904-213X
2812:0306-0012
2750:1359-7345
2706:0039-7881
2686:Synthesis
2651:0009-2665
2599:0009-2665
2552:0009-2665
2501:0947-6539
2462:189843060
2454:0026-9247
2407:0306-0012
2350:0001-4842
2303:0009-2665
2233:162570992
2198:520990503
2163:501315951
2128:0039-7911
1971:0009-2665
1863:0368-1769
1828:0002-7863
1691:1460-4744
1634:0001-4842
1595:1434-193X
1517:1460-4744
1468:405547697
1347:2374-7943
1234:0002-7863
1078:database.
1062:0368-1769
988:1433-7851
946:0009-2665
861:CC BY 2.5
838:cumulenes
793:peridinin
590:dihalides
498:≡
490:−
464:⇀
457:−
446:−
439:↽
367:Synthesis
224:propeller
147:cumulenes
143:allenylic
71:atom has
4976:See also
4911:Chloride
4837:Tellurol
4791:Selenium
4758:Xanthate
4472:Ammonium
4454:Nitrogen
4436:carbon,
4393:Carboxyl
4360:Aldehyde
4348:Acryloyl
4330:carbonyl
4234:hydrogen
4189:Cumulene
4007:97759274
3888:32267148
3782:36656952
3773:10462259
3616:23861294
3567:12108979
3528:97529095
3396:16011326
3346:22271630
3307:19603781
3193:15387613
3146:15058962
3029:20518460
2947:12683778
2820:23034723
2758:21409186
2659:12683779
2607:21314182
2560:21391568
2509:21207554
2415:20111793
2358:19603781
2311:11749314
1994:"Allene"
1979:22111574
1789:31857913
1740:29052303
1699:26890605
1652:30640446
1525:20111793
1365:29974064
1261:14784717
1195:22308109
1092:(2007),
996:14991780
863:license.
831:See also
706:The two
699:Research
620:O, etc.)
533:= 24.7.
520:MAPP gas
275:planes).
206:Symmetry
188:pi bonds
186:and two
170:Geometry
90:or some
5023:Alkenes
5000:organic
4799:Selenol
4723:Sulfone
4676:Sulfide
4574:NONOate
4569:Nitroso
4559:Nitrite
4554:Nitrate
4544:Cyanate
4534:Nitrile
4519:Amidine
4514:Imidate
4484:Nitrene
4479:Hydrazo
4467:Enamine
4398:Acetoxy
4386:carboxy
4353:Benzoyl
4291:Epoxide
4274:Methoxy
4264:Alcohol
4218:Carbene
4152:Methine
3879:7294439
3830:8297713
3744:Science
3607:3814173
2076:: 202.
1890:: 203.
1780:6921087
1643:6497370
1356:6026781
1154:4085600
1132:Bibcode
886:allenes
775:in the
773:pigment
708:π-bonds
693:propyne
609:process
560:alkynes
377:propyne
200:methane
153:History
135:allylic
131:allenic
127:allenyl
123:C=C=CR−
61:allenes
4899:Iodide
4819:Selone
4663:Sulfur
4372:Ketone
4365:Ketene
4343:Acetyl
4298:Peroxy
4269:Alkoxy
4259:Acetal
4240:oxygen
4229:carbon
4213:Alkyne
4206:Benzyl
4201:Phenyl
4184:Allene
4179:Crotyl
4159:Alkene
4147:Bridge
4135:Pentyl
4120:Propyl
4110:Methyl
4005:
3917:
3886:
3876:
3868:
3827:
3819:
3801:Nature
3780:
3770:
3762:
3723:
3684:
3614:
3604:
3565:
3526:
3518:
3477:
3467:
3442:
3432:
3394:
3386:
3344:
3305:
3297:
3222:
3191:
3183:
3144:
3136:
3066:
3027:
3019:
2980:
2970:
2945:
2937:
2898:
2859:
2818:
2810:
2756:
2748:
2704:
2657:
2649:
2605:
2597:
2558:
2550:
2507:
2499:
2460:
2452:
2413:
2405:
2356:
2348:
2309:
2301:
2231:
2221:
2196:
2186:
2161:
2151:
2126:
2006:: 12.
1977:
1969:
1861:
1826:
1787:
1777:
1738:
1697:
1689:
1650:
1640:
1632:
1593:
1523:
1515:
1466:
1456:
1429:
1363:
1353:
1345:
1259:
1232:
1193:
1152:
1124:Nature
1102:
1060:
994:
986:
944:
734:, and
616:SiX, D
283:chiral
115:allene
108:C=C=CH
81:C=C=CR
69:carbon
18:Allene
4931:Other
4768:Boron
4738:Thial
4671:Thiol
4564:Nitro
4529:Imide
4509:Amide
4494:Oxime
4489:Imine
4462:Amine
4410:Ester
4377:Ynone
4281:Ether
4252:R-O-R
4227:Only
4169:Allyl
4164:Vinyl
4130:Butyl
4115:Ethyl
4105:Alkyl
4003:S2CID
3524:S2CID
2458:S2CID
1150:S2CID
876:IUPAC
675:from
584:from
562:with
4853:Halo
4338:Acyl
4238:and
4196:Aryl
3915:ISBN
3884:PMID
3866:ISSN
3817:ISSN
3778:PMID
3760:ISSN
3721:ISSN
3682:ISSN
3612:PMID
3563:PMID
3516:ISSN
3475:OCLC
3465:ISBN
3440:OCLC
3430:ISBN
3392:PMID
3384:ISSN
3342:PMID
3303:PMID
3295:ISSN
3220:ISBN
3189:PMID
3181:ISSN
3142:PMID
3134:ISSN
3064:ISSN
3025:PMID
3017:ISSN
2978:OCLC
2968:ISBN
2943:PMID
2935:ISSN
2896:ISSN
2857:ISSN
2816:PMID
2808:ISSN
2754:PMID
2746:ISSN
2702:ISSN
2690:2007
2655:PMID
2647:ISSN
2603:PMID
2595:ISSN
2556:PMID
2548:ISSN
2505:PMID
2497:ISSN
2450:ISSN
2411:PMID
2403:ISSN
2354:PMID
2346:ISSN
2307:PMID
2299:ISSN
2229:OCLC
2219:ISBN
2194:OCLC
2184:ISBN
2159:OCLC
2149:ISBN
2124:ISSN
1975:PMID
1967:ISSN
1859:ISSN
1824:ISSN
1785:PMID
1736:PMID
1695:PMID
1687:ISSN
1648:PMID
1630:ISSN
1591:ISSN
1579:2004
1521:PMID
1513:ISSN
1464:OCLC
1454:ISBN
1427:ISBN
1361:PMID
1343:ISSN
1257:PMID
1230:ISSN
1191:PMID
1100:ISBN
1058:ISSN
992:PMID
984:ISSN
942:ISSN
857:text
791:and
667:and
270:and
137:and
63:are
4504:Azo
3993:doi
3963:doi
3935:doi
3907:doi
3874:PMC
3858:doi
3854:142
3825:PMC
3809:doi
3805:586
3768:PMC
3752:doi
3748:379
3713:doi
3709:121
3674:doi
3643:doi
3602:PMC
3594:doi
3555:doi
3506:doi
3376:doi
3372:105
3334:doi
3287:doi
3256:doi
3212:doi
3173:doi
3126:doi
3095:doi
3056:doi
3009:doi
3005:110
2927:doi
2923:103
2888:doi
2847:doi
2798:hdl
2790:doi
2738:doi
2694:doi
2639:doi
2635:103
2587:doi
2583:111
2540:doi
2536:111
2489:doi
2442:doi
2438:142
2393:hdl
2385:doi
2338:doi
2291:doi
2287:100
2260:doi
2116:doi
2078:doi
2045:doi
2008:doi
1959:doi
1955:112
1928:doi
1892:doi
1851:doi
1816:doi
1812:117
1775:PMC
1767:doi
1726:doi
1679:doi
1638:PMC
1622:doi
1583:doi
1552:doi
1503:hdl
1495:doi
1419:doi
1388:doi
1351:PMC
1335:doi
1298:hdl
1288:doi
1222:doi
1181:doi
1140:doi
1128:135
1050:doi
1023:doi
976:doi
934:doi
890:doi
888:".
779:of
663:in
643:of
55:In
5019::
4236:,
4231:,
4001:.
3989:60
3987:.
3983:.
3959:13
3957:.
3913:.
3882:.
3872:.
3864:.
3852:.
3848:.
3823:.
3815:.
3803:.
3799:.
3776:.
3766:.
3758:.
3746:.
3742:.
3719:.
3707:.
3703:.
3680:.
3670:31
3668:.
3664:.
3639:31
3637:.
3633:.
3610:.
3600:.
3590:52
3588:.
3584:.
3561:.
3551:31
3549:.
3545:.
3522:.
3514:.
3502:78
3500:.
3496:.
3473:.
3438:.
3390:.
3382:.
3370:.
3366:.
3354:^
3340:.
3330:51
3328:.
3324:.
3301:.
3293:.
3283:42
3281:.
3277:.
3252:40
3250:.
3246:.
3234:^
3218:.
3210:.
3187:.
3179:.
3169:69
3167:.
3163:.
3140:.
3132:.
3122:69
3120:.
3116:.
3091:62
3089:.
3085:.
3062:.
3052:98
3050:.
3046:.
3023:.
3015:.
3003:.
2999:.
2976:.
2941:.
2933:.
2921:.
2917:.
2894:.
2884:27
2882:.
2878:.
2855:.
2843:17
2841:.
2837:.
2814:.
2806:.
2796:.
2786:42
2784:.
2780:.
2766:^
2752:.
2744:.
2734:47
2732:.
2728:.
2714:^
2700:.
2688:.
2684:.
2667:^
2653:.
2645:.
2633:.
2629:.
2615:^
2601:.
2593:.
2581:.
2577:.
2554:.
2546:.
2534:.
2530:.
2503:.
2495:.
2485:17
2483:.
2479:.
2456:.
2448:.
2436:.
2432:.
2409:.
2401:.
2391:.
2381:39
2379:.
2375:.
2352:.
2344:.
2334:42
2332:.
2328:.
2305:.
2297:.
2285:.
2281:.
2256:40
2254:.
2250:.
2227:.
2192:.
2157:.
2122:.
2112:12
2110:.
2106:.
2085:;
2074:62
2072:.
2066:.
2041:63
2039:.
2015:;
2004:42
2002:.
1996:.
1973:.
1965:.
1953:.
1949:.
1920:.
1899:;
1888:63
1886:.
1880:.
1857:.
1845:.
1822:.
1810:.
1806:.
1783:.
1773:.
1761:.
1757:.
1734:.
1722:56
1720:.
1716:.
1693:.
1685:.
1675:45
1673:.
1669:.
1646:.
1636:.
1628:.
1618:52
1616:.
1612:.
1589:.
1577:.
1573:.
1548:40
1546:.
1542:.
1519:.
1511:.
1501:.
1491:39
1489:.
1485:.
1462:.
1425:.
1386:.
1382:.
1359:.
1349:.
1341:.
1329:.
1325:.
1296:.
1282:.
1278:.
1253:36
1251:.
1228:.
1218:74
1216:.
1212:.
1189:.
1177:51
1175:.
1171:.
1148:.
1138:.
1126:.
1122:.
1056:.
1044:.
1019:20
1013:.
990:.
982:.
972:43
970:.
966:.
954:^
940:.
930:67
928:.
924:.
912:^
900:^
878:,
736:16
732:14
730:,
728:12
724:15
720:13
713:11
669:10
566:,
531:eq
524:G°
502:CH
421:CH
379::
355:CH
324:or
320:2d
232:2d
218:CH
149:.
59:,
4077:e
4070:t
4063:v
4036:7
4009:.
3995::
3969:.
3965::
3941:.
3937::
3923:.
3909::
3890:.
3860::
3833:.
3811::
3784:.
3754::
3727:.
3715::
3688:.
3676::
3649:.
3645::
3618:.
3596::
3569:.
3557::
3530:.
3508::
3481:.
3446:.
3398:.
3378::
3348:.
3336::
3309:.
3289::
3262:.
3258::
3228:.
3214::
3195:.
3175::
3148:.
3128::
3101:.
3097::
3070:.
3058::
3031:.
3011::
2984:.
2949:.
2929::
2902:.
2890::
2863:.
2849::
2822:.
2800::
2792::
2760:.
2740::
2708:.
2696::
2661:.
2641::
2609:.
2589::
2562:.
2542::
2511:.
2491::
2464:.
2444::
2417:.
2395::
2387::
2360:.
2340::
2313:.
2293::
2266:.
2262::
2235:.
2200:.
2165:.
2130:.
2118::
2092:.
2080::
2051:.
2047::
2022:.
2010::
1981:.
1961::
1935:.
1930::
1906:.
1894::
1865:.
1853::
1830:.
1818::
1791:.
1769::
1763:9
1742:.
1728::
1701:.
1681::
1654:.
1624::
1597:.
1585::
1558:.
1554::
1527:.
1505::
1497::
1470:.
1435:.
1421::
1400:.
1390::
1367:.
1337::
1331:4
1306:.
1300::
1290::
1284:4
1263:.
1236:.
1224::
1197:.
1183::
1156:.
1142::
1134::
1064:.
1052::
1029:.
1025::
998:.
978::
948:.
936::
892::
840:.
812:2
810:)
808:3
804:η
681:7
677:8
665:9
657:6
653:5
649:4
636:3
618:2
614:3
579:N
574:)
551:(
528:K
494:C
486:C
478:3
474:H
425:2
416:=
412:C
408:=
404:C
396:2
392:H
357:2
342:E
340:(
329:2
318:D
295:B
291:A
272:S
268:R
228:2
220:2
121:2
119:R
110:2
106:2
104:H
102:(
88:H
83:2
79:2
77:R
41:.
34:.
20:)
Text is available under the Creative Commons Attribution-ShareAlike License. Additional terms may apply.
