108:
148:
588:
531:
510:
554:
539:
199:
227:
431:
484:
207:
322:
339:
608:
359:
267:
235:
310:
465:
569:
329:
Diazoketones can be synthesized in one-step from readily available ketones or carboxylic acid precursors by the addition of diazomethane to acyl chlorides. A diazo group transfer method can be used to produce α,ÎČ-unsaturated ketones. The traditional method of the deformylative diazo transfer approach
155:
The modified
Danheiser benzannulation allows the synthesis of polycyclic aromatic and heteroaromatic systems. This also includes naphthalenes, benzofurans and indoles. This second generation aromatic annulation is achieved by irradiation of a solution of acetylene and a vinyl or aryl α-diazo ketone
218:
cleavage generating a vinyl ketene which reacts with an acetylene in a regiospecific cycloaddition (Scheme 4). Reversible electrocyclic cleavage of the 2-vinylcyclobutenone yields a dienylketene. The dienylketene then undergoes a six-electron electrocyclization to give a hexadienone intermediate
222:
In the case of the modified benzannulation reaction (Scheme 5); irradiation of the diazoketones induces the Wolff rearrangement yielding the vinyl ketene intermediate which reacts with the acetylene in a cycloaddition then a four-electron cleavage of the resulting 4-substituted cyclobutenone
317:
Activated alkyoxyacetylenes can be synthesized in a single-pot preparation of triisopropylsilyloxyacetylenes from esters. The silyloxyacetylenes are useful substitutes for alkoxyacetylenes in cycloaddition reactions with ketenes and vinylketenes affording cyclobutenones (Scheme 8).
505:
metabolite that was originally prepared via a key benzannulation step. An alkyne and a cyclobutenone were reacted to form a substituted phenol in a single step in a 73% yield (Scheme 14). Mycophenolic acid was prepared in nine steps in an overall yield of 17-19%.
164:
of a diazoketone to generate an aryl or vinylketene. These ketene intermediates cannot be isolated due to their high reactivity to form diketenes. These rearrangements are performed in the presence of unsaturated compounds which undergo cycloadditions with the
119:
annulation. This annulation provides an efficient route to form an aromatic ring in one step. It is a thermal combination of a substituted cyclobutenones with heterosubstituted acetylenes to produce highly substituted aromatic compounds, specifically phenols or
854:
Mak, X. Y., Crombie, L. A., Danheiser, R. L. âSynthesis of
Polycyclic Benzofused Nitrogen Heterocycles via a Tandem Ynamide Benzannulation/Ring-Closing Metathesis Strategy. Application in a Formal Total Synthesis of (+)-FR900482.â J. Org. Chem. 2011, 76,
595:
An outstanding application of
Danheiser benzannulation in 6-step synthesis of dictyodendrins was demonstrated by Zhang and Ready. They obtained the cyclobutenone substrate using a hetero- cycloaddition between aryl ynol ethers (aryl
334:
enolates for the
Claisen formylation step. The key step in this procedure is activation of the ketone starting material to the corresponding α-trifluoroacetyl derivative using trifluoroethyltrifluoroacetate (TFEA) (Scheme 9).
98:
requires precursors that are often unstable to metallating reagents. Both these synthetic routes pose issues in total synthesis. In 1984 a new synthetic strategy was developed by Rick
Danheiser to address these shortcomings.
426:
for a solvent dependent benzannulation reaction (Scheme 11). In dichloromethane the ratio of A:B is 78:22 with an overall combined yield of 90% and in THF the ratio has switched to 7:93 (A:B) with a combined yield of 85%.
441:-catalyzed benzannulations have been developed using allylic compounds and alkynes. This palladium catalyzed reaction has been performed in both inter- and intramolecular forms. The cationic palladium complex (BF
864:
Smith, A.B., III, Adams, C. M., Kozmin, S. A., Paone, D. V. âTotal
Synthesis of (â)-Cylindrocyclophanes A and F Exploiting the Reversible Nature of Olefin Cross Metathesis Reaction. J. Am. Chem. Soc. 2001, 123,
346:
Alkynes or ketenophiles can be synthesized by various methods. Trialkylsilyloxyalkynes have proven to be excellent ketenophiles. These alkynes react in the annulation reaction to form resorcinol monosilyl
678:, Brisbois, R G. James, J. Kowalczyk, Miller, R. F. âAn Annulation Method for the Synthesis of Highly Substituted Polycyclic Aromatic and Heteroaromatic Compounds.â J. Am. Chem. Soc. 1990, 112, 3093-3100.
390:
Alkynyl ethers and siloxyacetylenes have proven to be the ideal pair for aromatic annulations. The reactions can be run with both activated heterosubstituted alkynes and un-activated acetlyenes. Alkynyl
741:
Kowaiski, C. J., Lak, S. G. âCycloadditions
Reactions of Silyloxyacetylenes with Ketenes: Synthesis of Cyclobutenones, Resorcinols, and Î-6-Tetrahydrocannabinol.â J. Am. Chem. Soc. 1988, 110, 3693-3695.
845:
Lam, T. Y., Wang, Y., Danheiser, R. L. âBenzannulation via the
Reaction of Ynamides and Vinylketenes. Application to the Synthesis of Highly Substituted Indoles.â J. Org. Chem. 2013, 78, 9396â9414.
124:(Scheme 1). This benzannulation reaction creates previously unaccessed aromatic substitution patterns. A variety of substituted aromatic rings can be prepared using this method including: phenols,
274:
For the second generation reaction starting with the diazoketone, the reaction is performed by irradiation of a 0.7 M solution of the ketone with 1.0-1.2 equivalents of acetylene. A low-pressure
527:
position can be functionalized with various substituents. Following the benzannulation reaction with various heterocyclization reactions can provide access to substituted indoles (Scheme 15).
175:
to generate a substituted aromatic ring (Scheme 2). Avoiding the use of the high energy cyclobutenone starting materials provides access to a wider variety of substituted aromatic compounds.
107:
604:
cole of dictyodendrins F, H and I. The successful usage of
Danheiser benzannulation allows Zhang and Ready to achieve the so-far shortest synthesis of dictyodendrin natural products.
561:
Kowalski used the benzannulation reaction with siloxyacetylenes for the first time, reacting them with cyclobutenones to synthesize a substituted phenol for the total synthesis of Î-6-
1988:
517:
In the synthesis of highly substituted indoles performed by
Danheiser, the key step was a benzannulation reaction using cyclobutenone and ynamides to produce highly substituted
147:
4203:
587:
704:
806:
Danheiser, R.L., Nishida, A., Savariar, S., Trova, M. P. âTrialkylsiloxyalkynes: Synthesis and Aromatic Annulation Reactions. Tetrahedron Lett. 1988, 29, 4917-4920.
530:
223:
produces a dienylketene which then undergoes a six-electron electrocyclization to give the 2,4-cyclohexanedione which tautomerizes to the final aromatic product.
226:
580:
specifically (â)-Cylindrocyclophane F. He utilized the reaction of a siloxyalkyne and a cyclobutenone to construct the dihydroxyl aromatic intermediate for an
827:
Tsukada, N., Sugawara, S., Nakaoka, K., Inoue, Y. âPalladium-Catalyzed Benzannulation from Alkynes and Allylic Compounds.â J. Org. Chem. 2003, 68, 5961-5966.
509:
214:
The reaction proceeds via a cascade of four subsequent pericyclic reactions (Scheme 3). Heating a cyclobutenone above 80 °C initiates a four-electron
453:
forming the aromatic compound 1-methyl-2,3,4,5-tetrapropylbenzene (Scheme 12). It was determined that the presence of exactly one equivalent of palladium
794:
Danheiser, R.L., Miller, R. F., Brisbois, R. G., Park, S. Z. âAn Improved Method for the Synthesis of α-Diazoketones.â J. Org. Chem. 1990, 55, 1959-1964.
321:
190:
to an alkyne or alkene (more specifically in the DÓ§tz reaction a carbene coordinated to a metal carbonyl group) to produce substituted aromatic phenols.
751:
3319:
3264:
627:
553:
338:
198:
4032:
3374:
3524:
2158:
727:
Danheiser, R. L., Gee, S. K. âRegiocontrolled Annulation Approach to Highly Substituted Aromatic Compounds.â J. Org. Chem. 1984, 49, 1672-1674.
4253:
4027:
1853:
989:
Zhang, Wenhan; Ready, Joseph M. (2017). "Total synthesis of the dictyodendrins as an arena to highlight emerging synthetic technologies".
3129:
1050:
59:
systems from acyclic precursors in a single step, with many substituents already in place. A common synthetic annulation reaction is the
568:
430:
302:
Cyclobutenone was originally synthesized from the 3-bromocyclobutanone and 3-chlorocyclobutanone precursors which were prepared from an
206:
3699:
2899:
1643:
776:
DÓ§tz, K. H. âSynthesis of Naphthol Skeleton from Pentacarbonyk chromium(0) and Tolan.â Angew. Chem. Internat. Edit. 1975, 14, 644-645.
3864:
3794:
3774:
3269:
2436:
1898:
2317:
1873:
546:
Danheiser also used the benzannulation with ynamides for the synthesis of polycyclic benzofused nitrogen heterocycles followed by
464:
1086:
457:(from which the allyl group adds into the final aromatic structure) is crucial for the catalyzed benzannulation to occur in good
3619:
4097:
4047:
2451:
815:
PĂŒnner, F., Hilt, G. âRegioselective Solvent-dependent Benzannulation of Conjugated Enynes.â Chem. Commun. 2012, 48, 3617â3619.
355:
of (Z)-2-halovinyl ethers to form alkoxyacetylenes is one of the most well established routes of alkyne synthesis (Scheme 10).
3554:
358:
4193:
4002:
3659:
3639:
3599:
2406:
1349:
278:
at 254 nm in a photochemical reactor is used for 5â8 hours until all the diazoketone has been consumed as determined by
266:
63:. It is a useful reactions for forming six-membered rings and generating polycyclic compounds. It is the combination of the
4188:
4118:
4017:
3674:
3529:
3159:
3004:
2614:
2241:
2018:
538:
701:
4268:
4052:
3364:
2854:
2529:
3074:
4263:
3977:
3839:
3629:
3594:
55:
precursors resulting in the fusion of a new ring via two newly generated bonds. These strategies can be used to create
483:
4153:
4092:
3624:
3539:
3509:
3489:
3354:
3349:
2724:
2649:
2292:
2246:
2113:
1374:
415:
836:
Danheiser, R. L., Gee, S. K., Perez, J. J. âTotal Synthesis of Mycophenolic Acid.â J. Am. Chem. Soc. 1986, 108, 807.
309:
4258:
4218:
4168:
3844:
3644:
3394:
3324:
1813:
1384:
3459:
2352:
2073:
4012:
3854:
3724:
3719:
3534:
3009:
2919:
2509:
2441:
2332:
1908:
1663:
1588:
1043:
414:(THF), unsymmetrical benzannulation products were obtained with good regioselectivity. These reactions utilize
3769:
4298:
4183:
4082:
4022:
3669:
3464:
3424:
3399:
3309:
2769:
1803:
1733:
1369:
1299:
2889:
4288:
3874:
3764:
3384:
3109:
2894:
2839:
2684:
2644:
2476:
2231:
1948:
1798:
4248:
3809:
3254:
764:
688:
263:
the ester side product formed from the reaction of the phenolic product with excess vinylketene (Scheme 6).
4283:
4198:
4173:
4148:
4133:
4057:
3972:
3869:
3829:
3694:
3649:
3414:
2959:
2944:
2809:
2599:
2267:
2023:
1703:
1678:
1648:
1239:
877:"The Ketene-Surrogate Coupling: Catalytic Conversion of Aryl Iodides into Aryl Ketenes through Ynol Ethers"
306:
and a ketene via two independent routes. Scheme 7 shows the preparation from cyclobutenone from an allene.
234:
4233:
4178:
4123:
3834:
3754:
3654:
3369:
3334:
3179:
3069:
2784:
2779:
2604:
2564:
2461:
2272:
2236:
2088:
2078:
1933:
1793:
1653:
1603:
1598:
1573:
1533:
1479:
1244:
1234:
1209:
4347:
4208:
3909:
3714:
3149:
3034:
2714:
2689:
2629:
2486:
2221:
1928:
1708:
1673:
1578:
1269:
1204:
1036:
934:"A Concise Total Synthesis of Dictyodendrins F, H, and I Using Aryl Ynol Ethers as Key Building Blocks"
523:
3499:
1763:
179:
4308:
4213:
4067:
3947:
3919:
3889:
3804:
3734:
3689:
3664:
3584:
3484:
3444:
3139:
2759:
2749:
2674:
2198:
2058:
2053:
2033:
1718:
1515:
1494:
1454:
1379:
247:
A typical Danheiser benzannulation reaction is run with a 0.4-2.0 M solution of the cyclobutenone in
1199:
4273:
4163:
4143:
4007:
3849:
3759:
3729:
3709:
3604:
3559:
3389:
3299:
3229:
3114:
3104:
2934:
2491:
2431:
2396:
2203:
2183:
2143:
1918:
1788:
1753:
1713:
1464:
1304:
1294:
1224:
251:
heated at 80-160 °C with a slight excess of the cyclobutenone. Upon addition of the alkyne a
3739:
4352:
4243:
4102:
3952:
3894:
3819:
3799:
3519:
3469:
3329:
3294:
3234:
3164:
2719:
2466:
2446:
2178:
2098:
1993:
1953:
1923:
1858:
1743:
1728:
1638:
1628:
1289:
1214:
1169:
547:
1504:
3982:
3704:
3454:
3434:
3409:
3359:
3274:
3249:
3204:
3174:
3154:
3124:
3089:
3044:
3019:
2994:
2879:
2804:
2584:
2277:
2213:
2013:
1738:
1658:
1344:
1319:
1096:
1091:
374:
in presence of excess cyclobutenone initiating the benzannulation reaction. Treatment with n-Bu
4318:
3904:
3859:
3574:
3544:
3514:
3449:
3429:
3344:
3339:
3304:
3259:
3244:
3239:
3219:
3209:
3144:
3134:
3064:
3014:
2534:
2337:
1913:
1868:
1698:
1688:
1434:
1359:
1154:
1116:
406:. This type of benzannulation involves a cycloaddition followed by a 1,3-hydrogen shift. In
84:
1364:
111:
Scheme 1: Danheiser Benzannulation Reaction of an Alkyne and a Cyclobutenone(X= OR, SR, NR2)
4087:
4037:
3987:
3967:
3957:
3814:
3789:
3504:
3494:
3379:
3194:
3189:
3119:
2904:
2704:
2664:
2594:
2559:
2514:
2481:
2347:
2322:
2302:
2123:
2083:
2043:
2008:
1938:
1693:
1563:
1538:
1076:
562:
477:
279:
171:
generated ketenes. When ketenes are formed in the presence of alkynes they proceed through
8:
4293:
4278:
3924:
3899:
3884:
3879:
3609:
3564:
3549:
3439:
3419:
3314:
3199:
3184:
3029:
2974:
2964:
2929:
2694:
2569:
2544:
2456:
2312:
2297:
2282:
2103:
2048:
1818:
1668:
1613:
1484:
1399:
1259:
1184:
577:
352:
256:
172:
161:
60:
52:
16:
Technique used to create highly substituted phenols in a single step in organic chemistry
4303:
2954:
2138:
1329:
219:
which rapidly tautomerizes to yield a highly substituted phenol or naphthol structures.
4042:
3992:
3962:
3824:
3614:
3404:
3289:
3224:
3214:
2979:
2909:
2874:
2869:
2849:
2844:
2789:
2699:
2549:
2411:
2401:
2307:
2093:
2038:
1968:
1888:
1783:
1683:
1618:
1543:
1389:
1254:
1189:
1174:
966:
933:
909:
876:
450:
291:
275:
3779:
3099:
2984:
2949:
2914:
2859:
2814:
2729:
2709:
2659:
2654:
2624:
2609:
2519:
2426:
2362:
2327:
2153:
2028:
1903:
1828:
1808:
1723:
1558:
1553:
1499:
1409:
1314:
1274:
1229:
1111:
1106:
1071:
1014:
1006:
971:
953:
914:
896:
675:
581:
496:
458:
28:
24:
2774:
637:
600:
precursors), and the following benzannulation enabled the rapid construction of the
4313:
4158:
4128:
4072:
3997:
3929:
3684:
3634:
3479:
3284:
3059:
3054:
2999:
2989:
2764:
2574:
2554:
2524:
2421:
2357:
2342:
2173:
2128:
2118:
2108:
2003:
1983:
1978:
1963:
1958:
1838:
1833:
1773:
1758:
1748:
1593:
1583:
1449:
1439:
1339:
1334:
1309:
1249:
1101:
1060:
998:
961:
945:
904:
888:
641:
632:
472:
This catalyzed reaction was also optimized for allyl substrates with catalytic CHCl
88:
64:
1429:
702:
Regioselective [4+2] Benzannulation: Synthesis of Polysubstituted Benzenes
4223:
3914:
3749:
3744:
3039:
3024:
2969:
2924:
2884:
2834:
2799:
2794:
2739:
2734:
2669:
2619:
2539:
2367:
2251:
2226:
2188:
2163:
2148:
2133:
2068:
1943:
1893:
1883:
1863:
1823:
1633:
1623:
1608:
1404:
1324:
1194:
1164:
1149:
1144:
711:." Chemistry Department. University of Illinois, 20 Nov. 2003. Web. 23 Nov. 2014.
708:
411:
407:
379:
283:
151:
Scheme 2:Danheiser Benzannulation Reaction with an α-Diazo Ketone(X= OR, SR, NR2)
785:
Sieja, J. B. âSynthesis of Cyclobutenone.â J. Am. Chem. Soc.1971, 93, 2481-2483.
4228:
4138:
4077:
3169:
3079:
3049:
2824:
2679:
2416:
2193:
2063:
1878:
1848:
1548:
1444:
1219:
1081:
230:
Scheme 5a:Mechanism for the Formation of the Vinyl Ketene (Wolff Rearrangement)
157:
133:
36:
1028:
4341:
4238:
3939:
3784:
3679:
3474:
2864:
2829:
2819:
2754:
2744:
2634:
2471:
2287:
1998:
1973:
1843:
1489:
1474:
1459:
1354:
1284:
1264:
1179:
1010:
957:
900:
636:, 2nd ed. (the "Gold Book") (1997). Online corrected version: (2006–) "
330:
has been improved upon by substituting the trifluoroacetylation of generated
252:
215:
183:
645:
3279:
2639:
2391:
2168:
1768:
1568:
1419:
1414:
1279:
1134:
1018:
975:
918:
892:
591:
Scheme 18: Benzannulation towards the Synthesis of (â)-Cylindrocyclophane F
607:
550:(Scheme 16) for the total synthesis of (+)-FR900482, an anticancer agent.
1778:
1424:
1394:
1159:
949:
501:
423:
125:
56:
576:
The benzannulation reaction was used by Smith in the total synthesis of
351:
which can be de-protected under mild reaction conditions. Base-promoted
325:
Scheme 8:Synthesis of Alkyoxyacetylenes and Conversion to Cyclobutenones
4062:
3589:
2939:
1002:
392:
287:
129:
121:
95:
48:
534:
Scheme15a: Benzannulation Towards the Synthesis of Substituted Indoles
601:
438:
395:
and ynamines have been used as reactants in the annulation reaction.
141:
572:
Scheme 17: Synthesis of Î-6-tetrahydrocannabinol via a Benzannulatio
342:
Scheme 9:Formation of Diazo Ketones by a Diazo Group Transfer Method
1469:
1139:
454:
260:
767:." Organic-Chemistry. Organic Chemistry Portal, Web. 09 Nov. 2014.
691:." Organic-Chemistry. Organic Chemistry Portal, Web. 06 Nov. 2014.
513:
Scheme 14:Benzannulation Toward the Synthesis of Mycophenolic Acid
1129:
518:
371:
367:
331:
248:
187:
167:
80:
32:
597:
446:
418:(dppp) substituted cobalt catalyst in the presence of powdered
403:
303:
137:
116:
752:
Strategic Applications of Named Reactions in Organic Synthesis
402:
have also been used for benzannulation reactions catalyzed by
87:
on aromatic precursors. However, these reactions can have low
410:, the symmetrical benzannulation products are yielded but in
399:
348:
202:
Scheme 3a: Reaction Mechanism of the Danheiser Benzannulation
68:
294:, are all appropriate solvents for the annulation reaction.
419:
557:
Scheme 16: Benzannulation Toward the Synthesis of FR900482
255:
occurs. The crude annulation product is treated with 10%
737:
735:
733:
468:
Scheme 12: Palladium catalyzed reaction with 4-octyne
382:
removes the siloxy groups to form the desired diols.
4204:
ErlenmeyerâPlöchl azlactone and amino-acid synthesis
730:
210:
Scheme 3b: Mechanism of the Benzannulation Reaction
491:
434:Scheme 11:Cobalt catalyzed Benzannulation Reaction
115:The Danheiser benzannulation is a regiocontrolled
3265:Divinylcyclopropane-cycloheptadiene rearrangement
4339:
1058:
3525:Thermal rearrangement of aromatic hydrocarbons
2159:Thermal rearrangement of aromatic hydrocarbons
932:Zhang, Wenhan; Ready, Joseph M. (2016-08-24).
802:
800:
723:
721:
719:
717:
671:
669:
667:
665:
663:
661:
659:
657:
655:
653:
449:when heated to 80 °C in the presence of
51:is defined as a transformation of one or more
4254:Lectka enantioselective beta-lactam synthesis
1514:
1044:
823:
821:
362:Scheme10:Synthesis of Trialkylsilyloxyalkynes
91:and are prone to over substitution. Directed
4033:Inverse electron-demand DielsâAlder reaction
1854:Heterogeneous metal catalyzed cross-coupling
606:
270:Scheme 6:Formation of the Ester Side Product
178:This reaction is quite complementary to the
3375:Lobry de BruynâVan Ekenstein transformation
797:
754:. Elsevier Inc.: Burlington, Massachusetts.
714:
650:
584:reaction to access the target (Scheme 18).
366:The synthesized alkynes are then heated in
160:. This reaction utilizes the photochemical
1051:
1037:
988:
931:
874:
818:
681:
3865:Petrenko-Kritschenko piperidone synthesis
3320:FritschâButtenbergâWiechell rearrangement
965:
908:
4028:Intramolecular DielsâAlder cycloaddition
938:Journal of the American Chemical Society
875:Zhang, Wenhan; Ready, Joseph M. (2014).
881:Angewandte Chemie International Edition
297:
74:
4340:
4048:Metal-centered cycloaddition reactions
3700:DebusâRadziszewski imidazole synthesis
1644:BodrouxâChichibabin aldehyde synthesis
242:
4194:Diazoalkane 1,3-dipolar cycloaddition
4098:Vinylcyclopropane (5+2) cycloaddition
4003:Diazoalkane 1,3-dipolar cycloaddition
3775:HurdâMori 1,2,3-thiadiazole synthesis
3270:DowdâBeckwith ring-expansion reaction
2437:HurdâMori 1,2,3-thiadiazole synthesis
1513:
1350:LFER solvent coefficients (data page)
1032:
3005:Sharpless asymmetric dihydroxylation
2242:Methoxymethylenetriphenylphosphorane
35:in a single step. It is named after
3130:AllenâMillarâTrippett rearrangement
313:Scheme 7:Synthesis of Cyclobutenone
13:
4269:Nitrone-olefin (3+2) cycloaddition
4264:Niementowski quinazoline synthesis
4053:Nitrone-olefin (3+2) cycloaddition
3978:Azide-alkyne Huisgen cycloaddition
3840:Niementowski quinazoline synthesis
3595:Azide-alkyne Huisgen cycloaddition
2900:MeerweinâPonndorfâVerley reduction
2452:LeimgruberâBatcho indole synthesis
633:Compendium of Chemical Terminology
586:
567:
552:
537:
529:
508:
482:
463:
429:
357:
337:
320:
308:
265:
233:
225:
205:
197:
146:
106:
14:
4364:
4093:Trimethylenemethane cycloaddition
3795:JohnsonâCoreyâChaykovsky reaction
3660:CadoganâSundberg indole synthesis
3640:BohlmannâRahtz pyridine synthesis
3600:BaeyerâEmmerling indole synthesis
2407:CadoganâSundberg indole synthesis
1899:JohnsonâCoreyâChaykovsky reaction
416:1,3-bis(diphenylphosphino)propane
4189:CookâHeilbron thiazole synthesis
4018:Hexadehydro DielsâAlder reaction
3845:Niementowski quinoline synthesis
3675:CookâHeilbron thiazole synthesis
3620:BischlerâMöhlau indole synthesis
3530:TiffeneauâDemjanov rearrangement
3160:BakerâVenkataraman rearrangement
2318:HornerâWadsworthâEmmons reaction
1989:Mizoroki-Heck vs. Reductive Heck
1874:HornerâWadsworthâEmmons reaction
1385:Neighbouring group participation
3725:Fiesselmann thiophene synthesis
3555:WestphalenâLettrĂ© rearrangement
3535:Vinylcyclopropane rearrangement
3365:KornblumâDeLaMare rearrangement
3010:Epoxidation of allylic alcohols
2920:Noyori asymmetric hydrogenation
2855:KornblumâDeLaMare rearrangement
2530:GallagherâHollander degradation
982:
925:
868:
858:
848:
839:
830:
809:
788:
779:
521:derivatives. In this case, the
492:Applications in Total Synthesis
83:were originally synthesized by
31:to generate highly substituted
4184:Chichibabin pyridine synthesis
3670:Chichibabin pyridine synthesis
3630:BlumâIttah aziridine synthesis
3465:Ring expansion and contraction
1734:Cross dehydrogenative coupling
770:
757:
744:
694:
621:
1:
4154:BischlerâNapieralski reaction
4112:Heterocycle forming reactions
3765:Hemetsberger indole synthesis
3625:BischlerâNapieralski reaction
3540:WagnerâMeerwein rearrangement
3510:SommeletâHauser rearrangement
3490:SeyferthâGilbert homologation
3355:IrelandâClaisen rearrangement
3350:HofmannâMartius rearrangement
3110:2,3-sigmatropic rearrangement
2725:CoreyâWinter olefin synthesis
2650:BartonâMcCombie deoxygenation
2293:CoreyâWinter olefin synthesis
2247:SeyferthâGilbert homologation
2114:SeyferthâGilbert homologation
750:KĂŒrti LĂĄszlĂł, Barbara CzakĂł.
614:
542:Scheme15b: Substituted Indole
487:Scheme 13 Palladium Catalyzed
476:and triphenylphosphine (dba =
445:) reacts with an excess of 4-
42:
4259:LehmstedtâTanasescu reaction
4219:GabrielâColman rearrangement
4174:Bucherer carbazole synthesis
4169:BorscheâDrechsel cyclization
4149:Bernthsen acridine synthesis
4134:Bamberger triazine synthesis
4119:AlgarâFlynnâOyamada reaction
3830:Nazarov cyclization reaction
3695:De Kimpe aziridine synthesis
3650:Bucherer carbazole synthesis
3645:BorscheâDrechsel cyclization
3415:Nazarov cyclization reaction
3395:MeyerâSchuster rearrangement
3325:GabrielâColman rearrangement
3075:WolffensteinâBöters reaction
2960:Reduction of nitro compounds
2810:Grundmann aldehyde synthesis
2615:AlgarâFlynnâOyamada reaction
2024:Olefin conversion technology
2019:NozakiâHiyamaâKishi reaction
1814:GabrielâColman rearrangement
1704:Claisen-Schmidt condensation
1649:Bouveault aldehyde synthesis
193:
39:who developed the reaction.
7:
4234:Hantzsch pyridine synthesis
4013:Enoneâalkene cycloadditions
3835:Nenitzescu indole synthesis
3755:Hantzsch pyridine synthesis
3720:FerrarioâAckermann reaction
3370:Kowalski ester homologation
3335:Halogen dance rearrangement
3180:Benzilic acid rearrangement
2605:Akabori amino-acid reaction
2565:Von Braun amide degradation
2510:BarbierâWieland degradation
2462:Nenitzescu indole synthesis
2442:KharaschâSosnovsky reaction
2333:JuliaâKocienski olefination
2237:Kowalski ester homologation
1934:Kowalski ester homologation
1909:JuliaâKocienski olefination
1664:CadiotâChodkiewicz coupling
1589:Aza-BaylisâHillman reaction
1534:Acetoacetic ester synthesis
1245:Dynamic binding (chemistry)
1235:Conrotatory and disrotatory
1210:Charge remote fragmentation
102:
10:
4369:
4299:RobinsonâGabriel synthesis
4249:Kröhnke pyridine synthesis
4083:Retro-DielsâAlder reaction
4023:Imine DielsâAlder reaction
3810:Kröhnke pyridine synthesis
3425:NewmanâKwart rearrangement
3400:MislowâEvans rearrangement
3310:FischerâHepp rearrangement
3255:Di-Ï-methane rearrangement
3035:Stephen aldehyde synthesis
2770:EschweilerâClarke reaction
2487:Williamson ether synthesis
1804:FujiwaraâMoritani reaction
1709:Combes quinoline synthesis
1674:Carbonyl olefin metathesis
1375:More O'FerrallâJencks plot
1300:GrunwaldâWinstein equation
1270:Electron-withdrawing group
1205:Catalytic resonance theory
4309:Urech hydantoin synthesis
4289:PomeranzâFritsch reaction
4214:Fischer oxazole synthesis
4111:
3948:1,3-Dipolar cycloaddition
3938:
3920:Urech hydantoin synthesis
3890:Reissert indole synthesis
3875:PomeranzâFritsch reaction
3805:Knorr quinoline synthesis
3735:Fischer oxazole synthesis
3665:Camps quinoline synthesis
3585:1,3-Dipolar cycloaddition
3573:
3485:Semipinacol rearrangement
3460:RambergâBĂ€cklund reaction
3445:Piancatelli rearrangement
3385:McFadyenâStevens reaction
3140:Alpha-ketol rearrangement
3088:
2895:McFadyenâStevens reaction
2840:KilianiâFischer synthesis
2760:Elbs persulfate oxidation
2685:BouveaultâBlanc reduction
2645:BaeyerâVilliger oxidation
2583:
2500:
2477:SchottenâBaumann reaction
2380:
2353:RambergâBĂ€cklund reaction
2260:
2232:KilianiâFischer synthesis
2212:
2074:RambergâBĂ€cklund reaction
2059:Pinacol coupling reaction
2054:Piancatelli rearrangement
1949:LiebeskindâSrogl coupling
1799:FujimotoâBelleau reaction
1522:
1516:List of organic reactions
1380:Negative hyperconjugation
1125:
1067:
4284:PictetâSpengler reaction
4199:EinhornâBrunner reaction
4164:Boger pyridine synthesis
4058:Oxo-DielsâAlder reaction
3973:Aza-DielsâAlder reaction
3870:PictetâSpengler reaction
3770:HofmannâLöffler reaction
3760:Hegedus indole synthesis
3730:Fischer indole synthesis
3605:Bartoli indole synthesis
3560:Willgerodt rearrangement
3390:McLafferty rearrangement
3300:Ferrier carbocyclization
3115:2,3-Wittig rearrangement
3105:1,2-Wittig rearrangement
2945:ParikhâDoering oxidation
2935:Oxygen rebound mechanism
2600:AdkinsâPeterson reaction
2492:Yamaguchi esterification
2432:Hegedus indole synthesis
2397:Bartoli indole synthesis
2268:BamfordâStevens reaction
2184:Weinreb ketone synthesis
2144:Stork enamine alkylation
1919:Knoevenagel condensation
1789:Ferrier carbocyclization
1679:CastroâStephens coupling
1305:Hammett acidity function
1295:Free-energy relationship
1240:CurtinâHammett principle
1225:Conformational isomerism
385:
21:Danheiser benzannulation
4244:Knorr pyrrole synthesis
4179:BuchererâBergs reaction
4124:AllanâRobinson reaction
4103:Wagner-Jauregg reaction
3895:Ring-closing metathesis
3820:Larock indole synthesis
3800:Knorr pyrrole synthesis
3655:BuchererâBergs reaction
3520:Stieglitz rearrangement
3500:SkattebĂžl rearrangement
3470:Ring-closing metathesis
3330:Group transfer reaction
3295:Favorskii rearrangement
3235:Cornforth rearrangement
3165:Bamberger rearrangement
3070:WolffâKishner reduction
2890:MarkĂłâLam deoxygenation
2785:FlemingâTamao oxidation
2780:FischerâTropsch process
2467:Oxymercuration reaction
2447:Knorr pyrrole synthesis
2273:BartonâKellogg reaction
2179:Wagner-Jauregg reaction
2099:Ring-closing metathesis
2089:ReimerâTiemann reaction
2079:RauhutâCurrier reaction
1994:Nef isocyanide reaction
1954:Malonic ester synthesis
1924:Knorr pyrrole synthesis
1859:High dilution principle
1794:FriedelâCrafts reaction
1729:Cross-coupling reaction
1654:BuchererâBergs reaction
1639:Blanc chloromethylation
1629:Blaise ketone synthesis
1604:BaylisâHillman reaction
1599:BartonâKellogg reaction
1574:AllanâRobinson reaction
1480:WoodwardâHoffmann rules
1215:Charge-transfer complex
991:Natural Product Reports
646:10.1351/goldbook.A00367
548:ring-closing metathesis
238:Scheme 5b: Vinyl Ketene
71:Condensation reaction.
4209:FeistâBenary synthesis
3983:Bradsher cycloaddition
3953:4+4 Photocycloaddition
3910:SimmonsâSmith reaction
3855:PaternĂČâBĂŒchi reaction
3715:FeistâBenary synthesis
3705:Dieckmann condensation
3455:Pummerer rearrangement
3435:Oxy-Cope rearrangement
3410:Myers allene synthesis
3360:Jacobsen rearrangement
3275:Electrocyclic reaction
3250:Demjanov rearrangement
3205:Buchner ring expansion
3175:Beckmann rearrangement
3155:Aza-Cope rearrangement
3150:ArndtâEistert reaction
3125:Alkyne zipper reaction
3045:Transfer hydrogenation
3020:Sharpless oxyamination
2995:Selenoxide elimination
2880:Lombardo methylenation
2805:Griesbaum coozonolysis
2715:CoreyâItsuno reduction
2690:BoylandâSims oxidation
2630:AngeliâRimini reaction
2278:Boord olefin synthesis
2222:ArndtâEistert reaction
2214:Homologation reactions
2014:Nitro-Mannich reaction
1929:KolbeâSchmitt reaction
1739:Cross-coupling partner
1659:Buchner ring expansion
1579:ArndtâEistert reaction
1345:Kinetic isotope effect
1092:Rearrangement reaction
893:10.1002/anie.201405036
611:
592:
573:
558:
543:
535:
514:
488:
469:
435:
363:
343:
326:
314:
271:
239:
231:
211:
203:
152:
112:
85:substitution reactions
4068:PausonâKhand reaction
3905:Sharpless epoxidation
3860:Pechmann condensation
3740:FriedlÀnder synthesis
3690:DavisâBeirut reaction
3545:Wallach rearrangement
3515:Stevens rearrangement
3450:Pinacol rearrangement
3430:Overman rearrangement
3345:Hofmann rearrangement
3340:Hayashi rearrangement
3305:Ferrier rearrangement
3260:Dimroth rearrangement
3245:Curtius rearrangement
3240:Criegee rearrangement
3220:Claisen rearrangement
3210:Carroll rearrangement
3145:Amadori rearrangement
3135:Allylic rearrangement
3015:Sharpless epoxidation
2750:DessâMartin oxidation
2675:BohnâSchmidt reaction
2535:Hofmann rearrangement
2338:Kauffmann olefination
2261:Olefination reactions
2199:WurtzâFittig reaction
2034:PalladiumâNHC complex
1914:Kauffmann olefination
1869:Homologation reaction
1719:CoreyâHouse synthesis
1699:Claisen rearrangement
1495:YukawaâTsuno equation
1455:SwainâLupton equation
1435:Spherical aromaticity
1370:MöbiusâHĂŒckel concept
1155:Aromatic ring current
1117:Substitution reaction
610:
590:
571:
556:
541:
533:
512:
486:
467:
433:
361:
341:
324:
312:
269:
237:
229:
209:
201:
150:
110:
4274:PaalâKnorr synthesis
4144:BartonâZard reaction
4088:Staudinger synthesis
4038:Ketene cycloaddition
4008:DielsâAlder reaction
3988:Cheletropic reaction
3968:Alkyne trimerisation
3850:PaalâKnorr synthesis
3815:Kulinkovich reaction
3790:Jacobsen epoxidation
3710:DielsâAlder reaction
3505:Smiles rearrangement
3495:Sigmatropic reaction
3380:Lossen rearrangement
3230:CoreyâFuchs reaction
3195:Boekelheide reaction
3190:Bergmann degradation
3120:Achmatowicz reaction
2905:Methionine sulfoxide
2705:Clemmensen reduction
2665:Bergmann degradation
2595:Acyloin condensation
2560:Strecker degradation
2515:Bergmann degradation
2482:Ullmann condensation
2348:Peterson olefination
2323:Hydrazone iodination
2303:Elimination reaction
2204:ZinckeâSuhl reaction
2124:Sonogashira coupling
2084:Reformatsky reaction
2044:Peterson olefination
2009:Nierenstein reaction
1939:Kulinkovich reaction
1754:DielsâAlder reaction
1714:CoreyâFuchs reaction
1694:Claisen condensation
1564:Alkyne trimerisation
1539:Acyloin condensation
1505:ÎŁ-bishomoaromaticity
1465:ThorpeâIngold effect
1077:Elimination reaction
950:10.1021/jacs.6b06460
563:tetrahydrocannabinol
478:dibenzylideneacetone
298:Reagent Preparations
173:pericyclic reactions
75:Reaction development
4294:Prilezhaev reaction
4279:Pellizzari reaction
3958:(4+3) cycloaddition
3925:Van Leusen reaction
3900:Robinson annulation
3885:Pschorr cyclization
3880:Prilezhaev reaction
3610:Bergman cyclization
3565:Wolff rearrangement
3550:Weerman degradation
3440:Pericyclic reaction
3420:Neber rearrangement
3315:Fries rearrangement
3200:Brook rearrangement
3185:Bergman cyclization
3030:Staudinger reaction
2975:Rosenmund reduction
2965:Reductive amination
2930:Oppenauer oxidation
2720:CoreyâKim oxidation
2695:Cannizzaro reaction
2570:Weerman degradation
2545:Isosaccharinic acid
2457:Mukaiyama hydration
2313:Hofmann elimination
2298:Dehydrohalogenation
2283:Chugaev elimination
2104:Robinson annulation
2049:Pfitzinger reaction
1819:Gattermann reaction
1764:WulffâDötz reaction
1744:DakinâWest reaction
1669:Carbonyl allylation
1614:Bergman cyclization
1400:Kennedy J. P. Orton
1320:Hammond's postulate
1290:FlippinâLodge angle
1260:Electromeric effect
1185:Beta-silicon effect
1170:BakerâNathan effect
944:(33): 10684â10692.
765:Wolff Rearrangement
689:Robinson Annulation
578:cylindrocyclophanes
353:dehydrohalogenation
257:potassium hydroxide
243:Reaction conditions
180:WulffâDötz reaction
162:Wolff rearrangement
61:Robinson annulation
4043:McCormack reaction
3993:Conia-ene reaction
3825:Madelung synthesis
3615:Biginelli reaction
3405:Mumm rearrangement
3290:Favorskii reaction
3225:Cope rearrangement
3215:Chan rearrangement
2980:Rubottom oxidation
2910:Miyaura borylation
2875:Lipid peroxidation
2870:Lindgren oxidation
2850:Kornblum oxidation
2845:Kolbe electrolysis
2790:Fukuyama reduction
2700:Carbonyl reduction
2550:Marker degradation
2412:Diazonium compound
2402:Boudouard reaction
2381:Carbon-heteroatom
2308:Grieco elimination
2094:Rieche formylation
2039:Passerini reaction
1969:Meerwein arylation
1889:Hydroxymethylation
1784:Favorskii reaction
1684:Chan rearrangement
1619:Biginelli reaction
1544:Aldol condensation
1390:2-Norbornyl cation
1365:Möbius aromaticity
1360:Markovnikov's rule
1255:Effective molarity
1200:BĂŒrgiâDunitz angle
1190:Bicycloaromaticity
1003:10.1039/C7NP00018A
707:2014-02-07 at the
612:
593:
574:
559:
544:
536:
515:
489:
470:
451:triphenylphosphine
436:
364:
344:
327:
315:
292:1,2-dichloroethane
276:mercury-vapor lamp
272:
240:
232:
212:
204:
153:
113:
4348:Organic reactions
4335:
4334:
4331:
4330:
4327:
4326:
4319:WohlâAue reaction
3963:6+4 Cycloaddition
3780:Iodolactonization
3100:1,2-rearrangement
3065:WohlâAue reaction
2985:Sabatier reaction
2950:Pinnick oxidation
2915:Mozingo reduction
2860:Leuckart reaction
2815:Haloform reaction
2730:Criegee oxidation
2710:Collins oxidation
2660:Benkeser reaction
2655:Bechamp reduction
2625:Andrussow process
2610:Alcohol oxidation
2520:Edman degradation
2427:Haloform reaction
2376:
2375:
2363:Takai olefination
2328:Julia olefination
2154:Takai olefination
2029:Olefin metathesis
1904:Julia olefination
1829:Grignard reaction
1809:Fukuyama coupling
1724:Coupling reaction
1689:ChanâLam coupling
1559:Alkyne metathesis
1554:Alkane metathesis
1410:Phosphaethynolate
1315:George S. Hammond
1275:Electronic effect
1230:Conjugated system
1112:Stereospecificity
1107:Stereoselectivity
1072:Addition reaction
1061:organic reactions
887:(34): 8980â8984.
700:Chung, Won-jin. "
582:olefin metathesis
497:Mycophenolic acid
37:Rick L. Danheiser
29:organic chemistry
25:chemical reaction
4360:
4314:Wenker synthesis
4304:Stollé synthesis
4159:Bobbitt reaction
4129:Auwers synthesis
4073:Povarov reaction
3998:Cyclopropanation
3936:
3935:
3930:Wenker synthesis
3685:Darzens reaction
3635:Bobbitt reaction
3480:Schmidt reaction
3285:Enyne metathesis
3060:Whiting reaction
3055:Wharton reaction
3000:Shapiro reaction
2990:Sarett oxidation
2955:Prévost reaction
2765:Emde degradation
2575:Wohl degradation
2555:Ruff degradation
2525:Emde degradation
2422:Grignard reagent
2358:Shapiro reaction
2343:McMurry reaction
2210:
2209:
2174:Ullmann reaction
2139:Stollé synthesis
2129:Stetter reaction
2119:Shapiro reaction
2109:Sakurai reaction
2004:Negishi coupling
1984:Minisci reaction
1979:Michael reaction
1964:McMurry reaction
1959:Mannich reaction
1839:Hammick reaction
1834:Grignard reagent
1774:Enyne metathesis
1759:Doebner reaction
1749:Darzens reaction
1594:Barbier reaction
1584:Auwers synthesis
1511:
1510:
1485:Woodward's rules
1450:Superaromaticity
1440:Spiroaromaticity
1340:Inductive effect
1335:Hyperconjugation
1310:Hammett equation
1250:Edwards equation
1102:Regioselectivity
1053:
1046:
1039:
1030:
1029:
1023:
1022:
997:(8): 1010â1034.
986:
980:
979:
969:
929:
923:
922:
912:
872:
866:
862:
856:
852:
846:
843:
837:
834:
828:
825:
816:
813:
807:
804:
795:
792:
786:
783:
777:
774:
768:
761:
755:
748:
742:
739:
728:
725:
712:
698:
692:
685:
679:
673:
648:
625:
89:regioselectivity
79:Polysubstituted
65:Michael Addition
4368:
4367:
4363:
4362:
4361:
4359:
4358:
4357:
4338:
4337:
4336:
4323:
4224:Gewald reaction
4107:
3934:
3915:Skraup reaction
3750:Graham reaction
3745:Gewald reaction
3576:
3569:
3091:
3084:
3040:Swern oxidation
3025:Stahl oxidation
2970:Riley oxidation
2925:Omega oxidation
2885:Luche reduction
2835:Jones oxidation
2800:Glycol cleavage
2795:Ganem oxidation
2740:Davis oxidation
2735:Dakin oxidation
2670:Birch reduction
2620:Amide reduction
2586:
2579:
2540:Hooker reaction
2502:
2496:
2384:
2382:
2372:
2368:Wittig reaction
2256:
2252:Wittig reaction
2227:Hooker reaction
2208:
2189:Wittig reaction
2164:Thorpe reaction
2149:Suzuki reaction
2134:Stille reaction
2069:Quelet reaction
1944:Kumada coupling
1894:Ivanov reaction
1884:Hydrovinylation
1864:Hiyama coupling
1824:Glaser coupling
1634:Blaise reaction
1624:Bingel reaction
1609:Benary reaction
1526:
1524:
1518:
1509:
1405:Passive binding
1325:Homoaromaticity
1175:Baldwin's rules
1150:Antiaromaticity
1145:Anomeric effect
1121:
1063:
1057:
1027:
1026:
987:
983:
930:
926:
873:
869:
863:
859:
853:
849:
844:
840:
835:
831:
826:
819:
814:
810:
805:
798:
793:
789:
784:
780:
775:
771:
762:
758:
749:
745:
740:
731:
726:
715:
709:Wayback Machine
699:
695:
686:
682:
676:Danheiser, R L.
674:
651:
626:
622:
617:
494:
480:) (Scheme 13).
475:
444:
412:tetrahydrofuran
408:dichloromethane
388:
380:tetrahydrofuran
377:
300:
284:Dichloromethane
259:in methanol to
245:
196:
134:benzothiophenes
105:
77:
45:
17:
12:
11:
5:
4366:
4356:
4355:
4353:Name reactions
4350:
4333:
4332:
4329:
4328:
4325:
4324:
4322:
4321:
4316:
4311:
4306:
4301:
4296:
4291:
4286:
4281:
4276:
4271:
4266:
4261:
4256:
4251:
4246:
4241:
4236:
4231:
4229:Hantzsch ester
4226:
4221:
4216:
4211:
4206:
4201:
4196:
4191:
4186:
4181:
4176:
4171:
4166:
4161:
4156:
4151:
4146:
4141:
4139:Banert cascade
4136:
4131:
4126:
4121:
4115:
4113:
4109:
4108:
4106:
4105:
4100:
4095:
4090:
4085:
4080:
4078:Prato reaction
4075:
4070:
4065:
4060:
4055:
4050:
4045:
4040:
4035:
4030:
4025:
4020:
4015:
4010:
4005:
4000:
3995:
3990:
3985:
3980:
3975:
3970:
3965:
3960:
3955:
3950:
3944:
3942:
3933:
3932:
3927:
3922:
3917:
3912:
3907:
3902:
3897:
3892:
3887:
3882:
3877:
3872:
3867:
3862:
3857:
3852:
3847:
3842:
3837:
3832:
3827:
3822:
3817:
3812:
3807:
3802:
3797:
3792:
3787:
3782:
3777:
3772:
3767:
3762:
3757:
3752:
3747:
3742:
3737:
3732:
3727:
3722:
3717:
3712:
3707:
3702:
3697:
3692:
3687:
3682:
3677:
3672:
3667:
3662:
3657:
3652:
3647:
3642:
3637:
3632:
3627:
3622:
3617:
3612:
3607:
3602:
3597:
3592:
3587:
3581:
3579:
3571:
3570:
3568:
3567:
3562:
3557:
3552:
3547:
3542:
3537:
3532:
3527:
3522:
3517:
3512:
3507:
3502:
3497:
3492:
3487:
3482:
3477:
3472:
3467:
3462:
3457:
3452:
3447:
3442:
3437:
3432:
3427:
3422:
3417:
3412:
3407:
3402:
3397:
3392:
3387:
3382:
3377:
3372:
3367:
3362:
3357:
3352:
3347:
3342:
3337:
3332:
3327:
3322:
3317:
3312:
3307:
3302:
3297:
3292:
3287:
3282:
3277:
3272:
3267:
3262:
3257:
3252:
3247:
3242:
3237:
3232:
3227:
3222:
3217:
3212:
3207:
3202:
3197:
3192:
3187:
3182:
3177:
3172:
3170:Banert cascade
3167:
3162:
3157:
3152:
3147:
3142:
3137:
3132:
3127:
3122:
3117:
3112:
3107:
3102:
3096:
3094:
3090:Rearrangement
3086:
3085:
3083:
3082:
3080:Zinin reaction
3077:
3072:
3067:
3062:
3057:
3052:
3050:Wacker process
3047:
3042:
3037:
3032:
3027:
3022:
3017:
3012:
3007:
3002:
2997:
2992:
2987:
2982:
2977:
2972:
2967:
2962:
2957:
2952:
2947:
2942:
2937:
2932:
2927:
2922:
2917:
2912:
2907:
2902:
2897:
2892:
2887:
2882:
2877:
2872:
2867:
2862:
2857:
2852:
2847:
2842:
2837:
2832:
2827:
2825:Hydrogenolysis
2822:
2817:
2812:
2807:
2802:
2797:
2792:
2787:
2782:
2777:
2775:Ătard reaction
2772:
2767:
2762:
2757:
2752:
2747:
2742:
2737:
2732:
2727:
2722:
2717:
2712:
2707:
2702:
2697:
2692:
2687:
2682:
2680:Bosch reaction
2677:
2672:
2667:
2662:
2657:
2652:
2647:
2642:
2637:
2632:
2627:
2622:
2617:
2612:
2607:
2602:
2597:
2591:
2589:
2585:Organic redox
2581:
2580:
2578:
2577:
2572:
2567:
2562:
2557:
2552:
2547:
2542:
2537:
2532:
2527:
2522:
2517:
2512:
2506:
2504:
2498:
2497:
2495:
2494:
2489:
2484:
2479:
2474:
2469:
2464:
2459:
2454:
2449:
2444:
2439:
2434:
2429:
2424:
2419:
2417:Esterification
2414:
2409:
2404:
2399:
2394:
2388:
2386:
2378:
2377:
2374:
2373:
2371:
2370:
2365:
2360:
2355:
2350:
2345:
2340:
2335:
2330:
2325:
2320:
2315:
2310:
2305:
2300:
2295:
2290:
2285:
2280:
2275:
2270:
2264:
2262:
2258:
2257:
2255:
2254:
2249:
2244:
2239:
2234:
2229:
2224:
2218:
2216:
2207:
2206:
2201:
2196:
2194:Wurtz reaction
2191:
2186:
2181:
2176:
2171:
2166:
2161:
2156:
2151:
2146:
2141:
2136:
2131:
2126:
2121:
2116:
2111:
2106:
2101:
2096:
2091:
2086:
2081:
2076:
2071:
2066:
2064:Prins reaction
2061:
2056:
2051:
2046:
2041:
2036:
2031:
2026:
2021:
2016:
2011:
2006:
2001:
1996:
1991:
1986:
1981:
1976:
1971:
1966:
1961:
1956:
1951:
1946:
1941:
1936:
1931:
1926:
1921:
1916:
1911:
1906:
1901:
1896:
1891:
1886:
1881:
1879:Hydrocyanation
1876:
1871:
1866:
1861:
1856:
1851:
1849:Henry reaction
1846:
1841:
1836:
1831:
1826:
1821:
1816:
1811:
1806:
1801:
1796:
1791:
1786:
1781:
1776:
1771:
1766:
1761:
1756:
1751:
1746:
1741:
1736:
1731:
1726:
1721:
1716:
1711:
1706:
1701:
1696:
1691:
1686:
1681:
1676:
1671:
1666:
1661:
1656:
1651:
1646:
1641:
1636:
1631:
1626:
1621:
1616:
1611:
1606:
1601:
1596:
1591:
1586:
1581:
1576:
1571:
1566:
1561:
1556:
1551:
1549:Aldol reaction
1546:
1541:
1536:
1530:
1528:
1523:Carbon-carbon
1520:
1519:
1508:
1507:
1502:
1500:Zaitsev's rule
1497:
1492:
1487:
1482:
1477:
1472:
1467:
1462:
1457:
1452:
1447:
1445:Steric effects
1442:
1437:
1432:
1427:
1422:
1417:
1412:
1407:
1402:
1397:
1392:
1387:
1382:
1377:
1372:
1367:
1362:
1357:
1352:
1347:
1342:
1337:
1332:
1327:
1322:
1317:
1312:
1307:
1302:
1297:
1292:
1287:
1282:
1277:
1272:
1267:
1262:
1257:
1252:
1247:
1242:
1237:
1232:
1227:
1222:
1217:
1212:
1207:
1202:
1197:
1192:
1187:
1182:
1177:
1172:
1167:
1162:
1157:
1152:
1147:
1142:
1137:
1132:
1126:
1123:
1122:
1120:
1119:
1114:
1109:
1104:
1099:
1097:Redox reaction
1094:
1089:
1084:
1082:Polymerization
1079:
1074:
1068:
1065:
1064:
1056:
1055:
1048:
1041:
1033:
1025:
1024:
981:
924:
867:
857:
847:
838:
829:
817:
808:
796:
787:
778:
769:
756:
743:
729:
713:
693:
680:
649:
619:
618:
616:
613:
493:
490:
473:
442:
387:
384:
375:
299:
296:
244:
241:
195:
192:
158:dichloroethane
104:
101:
76:
73:
44:
41:
15:
9:
6:
4:
3:
2:
4365:
4354:
4351:
4349:
4346:
4345:
4343:
4320:
4317:
4315:
4312:
4310:
4307:
4305:
4302:
4300:
4297:
4295:
4292:
4290:
4287:
4285:
4282:
4280:
4277:
4275:
4272:
4270:
4267:
4265:
4262:
4260:
4257:
4255:
4252:
4250:
4247:
4245:
4242:
4240:
4239:Herz reaction
4237:
4235:
4232:
4230:
4227:
4225:
4222:
4220:
4217:
4215:
4212:
4210:
4207:
4205:
4202:
4200:
4197:
4195:
4192:
4190:
4187:
4185:
4182:
4180:
4177:
4175:
4172:
4170:
4167:
4165:
4162:
4160:
4157:
4155:
4152:
4150:
4147:
4145:
4142:
4140:
4137:
4135:
4132:
4130:
4127:
4125:
4122:
4120:
4117:
4116:
4114:
4110:
4104:
4101:
4099:
4096:
4094:
4091:
4089:
4086:
4084:
4081:
4079:
4076:
4074:
4071:
4069:
4066:
4064:
4061:
4059:
4056:
4054:
4051:
4049:
4046:
4044:
4041:
4039:
4036:
4034:
4031:
4029:
4026:
4024:
4021:
4019:
4016:
4014:
4011:
4009:
4006:
4004:
4001:
3999:
3996:
3994:
3991:
3989:
3986:
3984:
3981:
3979:
3976:
3974:
3971:
3969:
3966:
3964:
3961:
3959:
3956:
3954:
3951:
3949:
3946:
3945:
3943:
3941:
3940:Cycloaddition
3937:
3931:
3928:
3926:
3923:
3921:
3918:
3916:
3913:
3911:
3908:
3906:
3903:
3901:
3898:
3896:
3893:
3891:
3888:
3886:
3883:
3881:
3878:
3876:
3873:
3871:
3868:
3866:
3863:
3861:
3858:
3856:
3853:
3851:
3848:
3846:
3843:
3841:
3838:
3836:
3833:
3831:
3828:
3826:
3823:
3821:
3818:
3816:
3813:
3811:
3808:
3806:
3803:
3801:
3798:
3796:
3793:
3791:
3788:
3786:
3785:Isay reaction
3783:
3781:
3778:
3776:
3773:
3771:
3768:
3766:
3763:
3761:
3758:
3756:
3753:
3751:
3748:
3746:
3743:
3741:
3738:
3736:
3733:
3731:
3728:
3726:
3723:
3721:
3718:
3716:
3713:
3711:
3708:
3706:
3703:
3701:
3698:
3696:
3693:
3691:
3688:
3686:
3683:
3681:
3680:Cycloaddition
3678:
3676:
3673:
3671:
3668:
3666:
3663:
3661:
3658:
3656:
3653:
3651:
3648:
3646:
3643:
3641:
3638:
3636:
3633:
3631:
3628:
3626:
3623:
3621:
3618:
3616:
3613:
3611:
3608:
3606:
3603:
3601:
3598:
3596:
3593:
3591:
3588:
3586:
3583:
3582:
3580:
3578:
3575:Ring forming
3572:
3566:
3563:
3561:
3558:
3556:
3553:
3551:
3548:
3546:
3543:
3541:
3538:
3536:
3533:
3531:
3528:
3526:
3523:
3521:
3518:
3516:
3513:
3511:
3508:
3506:
3503:
3501:
3498:
3496:
3493:
3491:
3488:
3486:
3483:
3481:
3478:
3476:
3475:Rupe reaction
3473:
3471:
3468:
3466:
3463:
3461:
3458:
3456:
3453:
3451:
3448:
3446:
3443:
3441:
3438:
3436:
3433:
3431:
3428:
3426:
3423:
3421:
3418:
3416:
3413:
3411:
3408:
3406:
3403:
3401:
3398:
3396:
3393:
3391:
3388:
3386:
3383:
3381:
3378:
3376:
3373:
3371:
3368:
3366:
3363:
3361:
3358:
3356:
3353:
3351:
3348:
3346:
3343:
3341:
3338:
3336:
3333:
3331:
3328:
3326:
3323:
3321:
3318:
3316:
3313:
3311:
3308:
3306:
3303:
3301:
3298:
3296:
3293:
3291:
3288:
3286:
3283:
3281:
3278:
3276:
3273:
3271:
3268:
3266:
3263:
3261:
3258:
3256:
3253:
3251:
3248:
3246:
3243:
3241:
3238:
3236:
3233:
3231:
3228:
3226:
3223:
3221:
3218:
3216:
3213:
3211:
3208:
3206:
3203:
3201:
3198:
3196:
3193:
3191:
3188:
3186:
3183:
3181:
3178:
3176:
3173:
3171:
3168:
3166:
3163:
3161:
3158:
3156:
3153:
3151:
3148:
3146:
3143:
3141:
3138:
3136:
3133:
3131:
3128:
3126:
3123:
3121:
3118:
3116:
3113:
3111:
3108:
3106:
3103:
3101:
3098:
3097:
3095:
3093:
3087:
3081:
3078:
3076:
3073:
3071:
3068:
3066:
3063:
3061:
3058:
3056:
3053:
3051:
3048:
3046:
3043:
3041:
3038:
3036:
3033:
3031:
3028:
3026:
3023:
3021:
3018:
3016:
3013:
3011:
3008:
3006:
3003:
3001:
2998:
2996:
2993:
2991:
2988:
2986:
2983:
2981:
2978:
2976:
2973:
2971:
2968:
2966:
2963:
2961:
2958:
2956:
2953:
2951:
2948:
2946:
2943:
2941:
2938:
2936:
2933:
2931:
2928:
2926:
2923:
2921:
2918:
2916:
2913:
2911:
2908:
2906:
2903:
2901:
2898:
2896:
2893:
2891:
2888:
2886:
2883:
2881:
2878:
2876:
2873:
2871:
2868:
2866:
2865:Ley oxidation
2863:
2861:
2858:
2856:
2853:
2851:
2848:
2846:
2843:
2841:
2838:
2836:
2833:
2831:
2830:Hydroxylation
2828:
2826:
2823:
2821:
2820:Hydrogenation
2818:
2816:
2813:
2811:
2808:
2806:
2803:
2801:
2798:
2796:
2793:
2791:
2788:
2786:
2783:
2781:
2778:
2776:
2773:
2771:
2768:
2766:
2763:
2761:
2758:
2756:
2755:DNA oxidation
2753:
2751:
2748:
2746:
2745:Deoxygenation
2743:
2741:
2738:
2736:
2733:
2731:
2728:
2726:
2723:
2721:
2718:
2716:
2713:
2711:
2708:
2706:
2703:
2701:
2698:
2696:
2693:
2691:
2688:
2686:
2683:
2681:
2678:
2676:
2673:
2671:
2668:
2666:
2663:
2661:
2658:
2656:
2653:
2651:
2648:
2646:
2643:
2641:
2638:
2636:
2635:Aromatization
2633:
2631:
2628:
2626:
2623:
2621:
2618:
2616:
2613:
2611:
2608:
2606:
2603:
2601:
2598:
2596:
2593:
2592:
2590:
2588:
2582:
2576:
2573:
2571:
2568:
2566:
2563:
2561:
2558:
2556:
2553:
2551:
2548:
2546:
2543:
2541:
2538:
2536:
2533:
2531:
2528:
2526:
2523:
2521:
2518:
2516:
2513:
2511:
2508:
2507:
2505:
2499:
2493:
2490:
2488:
2485:
2483:
2480:
2478:
2475:
2473:
2472:Reed reaction
2470:
2468:
2465:
2463:
2460:
2458:
2455:
2453:
2450:
2448:
2445:
2443:
2440:
2438:
2435:
2433:
2430:
2428:
2425:
2423:
2420:
2418:
2415:
2413:
2410:
2408:
2405:
2403:
2400:
2398:
2395:
2393:
2390:
2389:
2387:
2383:bond forming
2379:
2369:
2366:
2364:
2361:
2359:
2356:
2354:
2351:
2349:
2346:
2344:
2341:
2339:
2336:
2334:
2331:
2329:
2326:
2324:
2321:
2319:
2316:
2314:
2311:
2309:
2306:
2304:
2301:
2299:
2296:
2294:
2291:
2289:
2288:Cope reaction
2286:
2284:
2281:
2279:
2276:
2274:
2271:
2269:
2266:
2265:
2263:
2259:
2253:
2250:
2248:
2245:
2243:
2240:
2238:
2235:
2233:
2230:
2228:
2225:
2223:
2220:
2219:
2217:
2215:
2211:
2205:
2202:
2200:
2197:
2195:
2192:
2190:
2187:
2185:
2182:
2180:
2177:
2175:
2172:
2170:
2167:
2165:
2162:
2160:
2157:
2155:
2152:
2150:
2147:
2145:
2142:
2140:
2137:
2135:
2132:
2130:
2127:
2125:
2122:
2120:
2117:
2115:
2112:
2110:
2107:
2105:
2102:
2100:
2097:
2095:
2092:
2090:
2087:
2085:
2082:
2080:
2077:
2075:
2072:
2070:
2067:
2065:
2062:
2060:
2057:
2055:
2052:
2050:
2047:
2045:
2042:
2040:
2037:
2035:
2032:
2030:
2027:
2025:
2022:
2020:
2017:
2015:
2012:
2010:
2007:
2005:
2002:
2000:
1999:Nef synthesis
1997:
1995:
1992:
1990:
1987:
1985:
1982:
1980:
1977:
1975:
1974:Methylenation
1972:
1970:
1967:
1965:
1962:
1960:
1957:
1955:
1952:
1950:
1947:
1945:
1942:
1940:
1937:
1935:
1932:
1930:
1927:
1925:
1922:
1920:
1917:
1915:
1912:
1910:
1907:
1905:
1902:
1900:
1897:
1895:
1892:
1890:
1887:
1885:
1882:
1880:
1877:
1875:
1872:
1870:
1867:
1865:
1862:
1860:
1857:
1855:
1852:
1850:
1847:
1845:
1844:Heck reaction
1842:
1840:
1837:
1835:
1832:
1830:
1827:
1825:
1822:
1820:
1817:
1815:
1812:
1810:
1807:
1805:
1802:
1800:
1797:
1795:
1792:
1790:
1787:
1785:
1782:
1780:
1777:
1775:
1772:
1770:
1767:
1765:
1762:
1760:
1757:
1755:
1752:
1750:
1747:
1745:
1742:
1740:
1737:
1735:
1732:
1730:
1727:
1725:
1722:
1720:
1717:
1715:
1712:
1710:
1707:
1705:
1702:
1700:
1697:
1695:
1692:
1690:
1687:
1685:
1682:
1680:
1677:
1675:
1672:
1670:
1667:
1665:
1662:
1660:
1657:
1655:
1652:
1650:
1647:
1645:
1642:
1640:
1637:
1635:
1632:
1630:
1627:
1625:
1622:
1620:
1617:
1615:
1612:
1610:
1607:
1605:
1602:
1600:
1597:
1595:
1592:
1590:
1587:
1585:
1582:
1580:
1577:
1575:
1572:
1570:
1567:
1565:
1562:
1560:
1557:
1555:
1552:
1550:
1547:
1545:
1542:
1540:
1537:
1535:
1532:
1531:
1529:
1525:bond forming
1521:
1517:
1512:
1506:
1503:
1501:
1498:
1496:
1493:
1491:
1490:Y-aromaticity
1488:
1486:
1483:
1481:
1478:
1476:
1475:Walsh diagram
1473:
1471:
1468:
1466:
1463:
1461:
1460:Taft equation
1458:
1456:
1453:
1451:
1448:
1446:
1443:
1441:
1438:
1436:
1433:
1431:
1430:ÎŁ-aromaticity
1428:
1426:
1423:
1421:
1418:
1416:
1413:
1411:
1408:
1406:
1403:
1401:
1398:
1396:
1393:
1391:
1388:
1386:
1383:
1381:
1378:
1376:
1373:
1371:
1368:
1366:
1363:
1361:
1358:
1356:
1355:Marcus theory
1353:
1351:
1348:
1346:
1343:
1341:
1338:
1336:
1333:
1331:
1330:HĂŒckel's rule
1328:
1326:
1323:
1321:
1318:
1316:
1313:
1311:
1308:
1306:
1303:
1301:
1298:
1296:
1293:
1291:
1288:
1286:
1285:Evelyn effect
1283:
1281:
1278:
1276:
1273:
1271:
1268:
1266:
1265:Electron-rich
1263:
1261:
1258:
1256:
1253:
1251:
1248:
1246:
1243:
1241:
1238:
1236:
1233:
1231:
1228:
1226:
1223:
1221:
1218:
1216:
1213:
1211:
1208:
1206:
1203:
1201:
1198:
1196:
1193:
1191:
1188:
1186:
1183:
1181:
1180:Bema Hapothle
1178:
1176:
1173:
1171:
1168:
1166:
1163:
1161:
1158:
1156:
1153:
1151:
1148:
1146:
1143:
1141:
1138:
1136:
1133:
1131:
1128:
1127:
1124:
1118:
1115:
1113:
1110:
1108:
1105:
1103:
1100:
1098:
1095:
1093:
1090:
1088:
1085:
1083:
1080:
1078:
1075:
1073:
1070:
1069:
1066:
1062:
1054:
1049:
1047:
1042:
1040:
1035:
1034:
1031:
1020:
1016:
1012:
1008:
1004:
1000:
996:
992:
985:
977:
973:
968:
963:
959:
955:
951:
947:
943:
939:
935:
928:
920:
916:
911:
906:
902:
898:
894:
890:
886:
882:
878:
871:
861:
851:
842:
833:
824:
822:
812:
803:
801:
791:
782:
773:
766:
760:
753:
747:
738:
736:
734:
724:
722:
720:
718:
710:
706:
703:
697:
690:
684:
677:
672:
670:
668:
666:
664:
662:
660:
658:
656:
654:
647:
643:
639:
635:
634:
629:
624:
620:
609:
605:
603:
599:
589:
585:
583:
579:
570:
566:
565:(Scheme 17).
564:
555:
551:
549:
540:
532:
528:
526:
525:
520:
511:
507:
504:
503:
498:
485:
481:
479:
466:
462:
460:
456:
452:
448:
440:
432:
428:
425:
421:
417:
413:
409:
405:
401:
396:
394:
383:
381:
373:
369:
360:
356:
354:
350:
340:
336:
333:
323:
319:
311:
307:
305:
295:
293:
289:
285:
281:
277:
268:
264:
262:
258:
254:
253:cycloaddition
250:
236:
228:
224:
220:
217:
216:electrocyclic
208:
200:
191:
189:
185:
184:cycloaddition
182:. This is a
181:
176:
174:
170:
169:
163:
159:
149:
145:
143:
139:
135:
131:
127:
123:
118:
109:
100:
97:
94:
90:
86:
82:
72:
70:
66:
62:
58:
54:
50:
40:
38:
34:
30:
26:
22:
3280:Ene reaction
2640:Autoxidation
2501:Degradation
2392:Azo coupling
2169:Ugi reaction
1769:Ene reaction
1569:Alkynylation
1420:Polyfluorene
1415:Polar effect
1280:Electrophile
1195:Bredt's rule
1165:Baird's rule
1135:Alpha effect
994:
990:
984:
941:
937:
927:
884:
880:
870:
860:
850:
841:
832:
811:
790:
781:
772:
759:
746:
696:
683:
631:
623:
594:
575:
560:
545:
522:
516:
500:
495:
471:
437:
397:
389:
365:
345:
328:
316:
301:
273:
246:
221:
213:
177:
166:
154:
126:naphthalenes
114:
92:
78:
46:
20:
18:
1779:Ethenolysis
1425:Ring strain
1395:Nucleophile
1220:Clar's rule
1160:Aromaticity
502:Penicillium
424:zinc iodide
398:Conjugated
130:benzofurans
122:resorcinols
4342:Categories
4063:Ozonolysis
3590:Annulation
2940:Ozonolysis
1059:Topics in
865:5925-5937.
855:1852â1873.
638:annulation
615:References
393:thioethers
288:chloroform
282:analysis.
142:carbazoles
96:metalation
49:annulation
43:Annulation
3577:reactions
3092:reactions
2587:reactions
2503:reactions
2385:reactions
1527:reactions
1011:0265-0568
958:0002-7863
901:1521-3773
602:carbazole
439:Palladium
194:Mechanism
1470:Vinylogy
1140:Annulene
1087:Reagents
1019:28737179
976:27471872
919:24975840
705:Archived
455:catalyst
261:saponify
103:Reaction
81:benzenes
67:and the
57:aromatic
27:used in
1130:A value
967:5006189
910:4134717
519:aniline
372:toluene
368:benzene
332:lithium
249:toluene
188:carbene
168:in situ
138:indoles
53:acyclic
33:phenols
1017:
1009:
974:
964:
956:
917:
907:
899:
598:ketene
447:octyne
404:cobalt
400:enynes
378:NF in
349:ethers
304:allene
290:, and
140:, and
117:phenol
628:IUPAC
524:ortho
499:is a
459:yield
386:Scope
186:of a
93:ortho
69:Aldol
23:is a
1015:PMID
1007:ISSN
972:PMID
954:ISSN
915:PMID
897:ISSN
422:and
420:zinc
19:The
999:doi
962:PMC
946:doi
942:138
905:PMC
889:doi
642:doi
640:".
370:or
280:TLC
156:in
47:An
4344::
1013:.
1005:.
995:34
993:.
970:.
960:.
952:.
940:.
936:.
913:.
903:.
895:.
885:53
883:.
879:.
820:^
799:^
732:^
716:^
652:^
630:,
461:.
286:,
144:.
136:,
132:,
128:,
1052:e
1045:t
1038:v
1021:.
1001::
978:.
948::
921:.
891::
763:"
687:"
644::
474:3
443:4
376:4
Text is available under the Creative Commons Attribution-ShareAlike License. Additional terms may apply.
