353:
221:
20:
382:
1023:
606:
1011:
602:β-Elimination, with loss of electrofuge and nucleofuge on vicinal carbon atoms, is by far the most common type of elimination. The ability to form a stable product containing a C=C or C=X bond, as well as orbital alignment considerations, strongly favors β-elimination over other elimination processes. However, other types are known, generally for systems where β-elimination cannot occur.
632:, as a reactive intermediate. On the other hand, formic acid undergoes α-elimination to afford the stable products water and carbon monoxide under acidic conditions. α-Elimination may also occur on a metal center, one particularly common result of which is lowering of both the metal oxidation state and coordination number by 2 units in a process known as
647:
In certain special cases, γ- and higher eliminations to form three-membered or larger rings is also possible in both organic and organometallic processes. For instance, certain Pt(II) complexes undergo γ- and δ-elimination to give metallocycles. More recently, γ-silyl elimination of a silylcyclobutyl
790:
In rare cases in which β hydrogens are unavailable but substitution is disfavored, α-elimination to form a carbene can sometimes occur. In particular: (1) Trihalomethanes like chloroform can react with NaOH to form dihalocarbenes (substitution is electronically disfavored). (2) Allyl and benzyl
963:
Kelly, Christopher B.; Colthart, Allison M.; Constant, Brad D.; Corning, Sean R.; Dubois, Lily N. E.; Genovese, Jacqueline T.; Radziewicz, Julie L.; Sletten, Ellen M.; Whitaker, Katherine R. (2011-04-01). "Enabling the
Synthesis of Perfluoroalkyl Bicyclobutanes via 1,3 Îł-Silyl Elimination".
59:. The numbers refer not to the number of steps in the mechanism, but rather to the kinetics of the reaction: E2 is bimolecular (second-order) while E1 is unimolecular (first-order). In cases where the molecule is able to stabilize an anion but possesses a poor
557:
2 substitution is hard to achieve when strong bases are used, as alkene products arising from elimination are almost always observed to some degree. On the other hand, clean E2 can be achieved by simply selecting a sterically hindered base (e.g., potassium
446:
being favored. Fluoride is not a good leaving group, so eliminations with fluoride as the leaving group have slower rates than other halogens . There is a certain level of competition between the elimination reaction and
531:> 11, e.g., hydroxide, alkoxide, acetylide), the result is generally elimination by E2, while weaker bases that are still good nucleophiles (e.g., acetate, azide, cyanide, iodide) will give primarily S
593:
2 reaction because in this reaction type the C-H bonds tighten in the transition state. The KIE's for the ethyl (0.99) and isopropyl (1.72) analogues suggest competition between the two reaction modes.
612:
The next most common type of elimination reaction is α-elimination. For a carbon center, the result of α-elimination is the formation of a carbene, which includes "stable carbenes" such as
2452:
928:
Moore, Stephen S.; DiCosimo, Robert; Sowinski, Allan F.; Whitesides, George M. (1981-02-01). "Ring strain in bis(triethylphosphine)-3,3-dimethylplatinacyclobutane is small".
566:
1 almost always result in a product mixture contaminated by some E1 product (again, with the exception of cases where the lack of β hydrogens makes elimination impossible).
826:
Stephanie M. Villano; Shuji Kato; Veronica M. Bierbaum (2006). "Deuterium
Kinetic Isotope Effects in Gas-Phase SN2 and E2 Reactions: Comparison of Experiment and Theory".
4667:
754:
Nash, J. J.; Leininger, M. A.; Keyes, K. (April 2008). "Pyrolysis of Aryl
Sulfonate Esters in the Absence of Solvent: E1 or E2? A Puzzle for the Organic Laboratory".
644:
refer to processes that result in formation of a metal-carbene complex. In these reactions, it is the carbon adjacent to the metal that undergoes α-elimination.)
791:
chloride can react with lithium tetramethylpiperide (LiTMP) to form vinylcarbene and phenylcarbene, respectively (substitution is sterically disfavored).
403:
Highly substituted carbocations are more stable than methyl or primary substituted cations. Such stability gives time for the two-step E1 mechanism to occur.
553:
In general, with the exception of reactions in which E2 is impossible because β hydrogens are unavailable (e.g. methyl, allyl, and benzyl halides), clean S
514:
2 reaction) to essentially only 1° haloalkanes; 2° haloalkanes generally do not give synthetically useful yields, while 3° haloalkanes fail completely.
3783:
3728:
4496:
502:
For example, when a 3° haloalkane is reacts with an alkoxide, due to strong basic character of the alkoxide and unreactivity of 3° group towards S
172:
conformation with higher energy. The reaction mechanism involving staggered conformation is more favorable for E2 reactions (unlike E1 reactions).
3838:
517:
With strong base, 3° haloalkanes give elimination by E2. With weak bases, mixtures of elimination and substitution products form by competing S
3988:
2622:
352:
4717:
1055:
400:
Highly substituted alkyl halides are bulky, limiting the room for the E2 one-step mechanism; therefore, the two-step E1 mechanism is favored.
4491:
2317:
315:
The reaction usually occurs in the complete absence of a base or the presence of only a weak base (acidic conditions and high temperature).
3593:
1514:
4163:
3363:
2107:
1027:
134:
It is typically undergone by primary substituted alkyl halides, but is possible with some secondary alkyl halides and other compounds.
4328:
4258:
4238:
3733:
2900:
2362:
2781:
2337:
1550:
4083:
4561:
4511:
2915:
1015:
304:
is influenced only by the concentration of the alkyl halide because carbocation formation is the slowest step, as known as the
4018:
4657:
4466:
4123:
4103:
4063:
2870:
1813:
4652:
4582:
4481:
4138:
3993:
3623:
3468:
3078:
2705:
2482:
4732:
4516:
3828:
3318:
2993:
1267:
1144:
3538:
4727:
4441:
4303:
4093:
4058:
1101:
4617:
4556:
4088:
4003:
3973:
3953:
3818:
3813:
3188:
3113:
2756:
2710:
2577:
1838:
1408:
1048:
904:
810:
731:
4722:
4682:
4632:
4308:
4108:
3858:
3788:
2277:
1848:
3923:
2816:
2537:
381:
220:
4476:
4318:
4188:
4183:
3998:
3473:
3383:
2973:
2905:
2796:
2372:
2127:
2052:
1507:
4233:
4816:
4811:
4762:
4647:
4546:
4486:
4133:
3928:
3888:
3863:
3773:
3233:
2267:
2197:
1833:
1763:
1316:
1311:
1121:
871:
148:
Because the E2 mechanism results in the formation of a pi bond, the two leaving groups (often a hydrogen and a
3353:
4752:
4338:
4228:
3848:
3573:
3358:
3303:
3148:
3108:
2940:
2695:
2412:
2262:
1481:
1476:
756:
4712:
4273:
3718:
4821:
4747:
4662:
4637:
4612:
4597:
4521:
4436:
4333:
4293:
4158:
4113:
3878:
3423:
3408:
3273:
3063:
2731:
2487:
2167:
2142:
2112:
1703:
1041:
535:
2. Finally, weakly nucleophilic species (e.g., water, alcohols, carboxylic acids) will give a mixture of S
51:
are removed from a molecule in either a one- or two-step mechanism. The one-step mechanism is known as the
550:
2 when the nucleophile is also unhindered. However, strongly basic and hindered nucleophiles favor E2.
4697:
4642:
4587:
4298:
4218:
4118:
3833:
3798:
3643:
3533:
3248:
3243:
3068:
3028:
2925:
2736:
2700:
2552:
2542:
2397:
2257:
2117:
2067:
2062:
2037:
1997:
1943:
1708:
1698:
1673:
506:
2, only alkene formation by E2 elimination is observed. Thus, elimination by E2 limits the scope of the
4672:
4373:
4178:
3613:
3498:
3178:
3153:
3093:
2950:
2685:
2392:
2172:
2137:
2042:
1733:
1668:
1500:
1446:
1136:
507:
3963:
2227:
4772:
4677:
4531:
4411:
4383:
4353:
4268:
4198:
4153:
4128:
4048:
3948:
3908:
3603:
3223:
3213:
3138:
2662:
2522:
2517:
2497:
2182:
1979:
1958:
1918:
1843:
1173:
1073:
669:
448:
64:
1663:
4737:
4627:
4607:
4471:
4313:
4223:
4193:
4173:
4068:
4023:
3853:
3763:
3693:
3578:
3568:
3398:
2955:
2895:
2860:
2667:
2647:
2607:
2382:
2252:
2217:
2177:
1928:
1768:
1758:
1688:
1403:
330:
309:
202:
4203:
4707:
4566:
4416:
4358:
4283:
4263:
3983:
3933:
3793:
3758:
3698:
3628:
3183:
2930:
2910:
2642:
2562:
2457:
2417:
2387:
2322:
2207:
2192:
2102:
2092:
1753:
1678:
1633:
1451:
1252:
657:
495:
1968:
4446:
4168:
3918:
3898:
3873:
3823:
3738:
3713:
3668:
3638:
3618:
3588:
3553:
3508:
3483:
3458:
3343:
3268:
3048:
2741:
2677:
2477:
2202:
2122:
1808:
1783:
1560:
1555:
1206:
570:
375:
161:
721:
4782:
4368:
4323:
4038:
4008:
3978:
3913:
3893:
3808:
3803:
3768:
3723:
3708:
3703:
3683:
3673:
3608:
3598:
3528:
3478:
2998:
2801:
2377:
2332:
2162:
2152:
1898:
1823:
1618:
1580:
1436:
1368:
1226:
1216:
633:
305:
198:
183:
142:
1828:
4551:
4501:
4451:
4431:
4421:
4278:
4253:
3968:
3958:
3843:
3658:
3653:
3583:
3368:
3168:
3128:
3058:
3023:
2978:
2945:
2811:
2786:
2587:
2547:
2507:
2472:
2402:
2157:
2027:
2002:
1431:
765:
294:
260:
E1 is a model to explain a particular type of chemical elimination reaction. E1 stands for
8:
4757:
4742:
4388:
4363:
4348:
4343:
4073:
4028:
4013:
3903:
3883:
3778:
3663:
3648:
3493:
3438:
3428:
3393:
3158:
3033:
3008:
2920:
2776:
2761:
2746:
2567:
2512:
2282:
2132:
2077:
1948:
1863:
1723:
1648:
1441:
1373:
1358:
1301:
4767:
3418:
2602:
1793:
769:
411:
1 and E1 pathways are competing, the E1 pathway can be favored by increasing the heat.
4506:
4456:
4426:
4288:
4078:
3868:
3753:
3688:
3678:
3443:
3373:
3338:
3333:
3313:
3308:
3253:
3163:
3013:
2875:
2865:
2771:
2557:
2502:
2432:
2352:
2247:
2147:
2082:
2007:
1853:
1718:
1653:
1638:
1466:
1236:
1065:
656:
Many of the concepts and terminology related to elimination reactions were proposed by
542:
For 1° haloalkanes with β-branching, E2 elimination is still generally preferred over S
237:
116:
4243:
3563:
3448:
3413:
3378:
3323:
3278:
3193:
3173:
3123:
3118:
3088:
3073:
2983:
2890:
2826:
2791:
2617:
2492:
2367:
2292:
2272:
2187:
2022:
2017:
1963:
1873:
1778:
1738:
1693:
1575:
1570:
1535:
1461:
1456:
1418:
1363:
1282:
1262:
1198:
989:
981:
945:
910:
900:
877:
867:
844:
828:
806:
737:
727:
690:
524:
The case of 2° haloalkanes is relatively complex. For strongly basic nucleophiles (p
249:
3238:
16:
Reaction where 2 substituents are removed from a molecule in a 1 or 2 step mechanism
4777:
4622:
4592:
4536:
4461:
4393:
4148:
4098:
3943:
3748:
3523:
3518:
3463:
3453:
3228:
3038:
3018:
2988:
2885:
2821:
2806:
2637:
2592:
2582:
2572:
2467:
2447:
2442:
2427:
2422:
2302:
2297:
2237:
2222:
2212:
2057:
2047:
1913:
1903:
1803:
1798:
1773:
1713:
1565:
1524:
1393:
1342:
1296:
973:
937:
836:
773:
699:
578:
471:
396:
E1 eliminations happen with highly substituted alkyl halides for two main reasons.
176:
157:
128:
44:
1893:
825:
573:(KIE) was determined for the gas phase reaction of several alkyl halides with the
4687:
4378:
4213:
4208:
3503:
3488:
3433:
3388:
3348:
3298:
3263:
3258:
3203:
3198:
3133:
3083:
3003:
2831:
2715:
2690:
2652:
2627:
2612:
2597:
2532:
2407:
2357:
2347:
2327:
2287:
2097:
2087:
2072:
1868:
1788:
1658:
1628:
1613:
1608:
1471:
1383:
1332:
625:
613:
582:
341:
216:
mechanism if the base can also act as a nucleophile (true for many common bases).
19:
4692:
4602:
4541:
3633:
3543:
3513:
3288:
3143:
2880:
2657:
2527:
2342:
2312:
2012:
1908:
1683:
1545:
1178:
1167:
153:
1492:
145:, because it's influenced by both the alkyl halide and the base (bimolecular).
4805:
4702:
4403:
4248:
4143:
3938:
3328:
3293:
3283:
3218:
3208:
3098:
2935:
2751:
2462:
2437:
2307:
1953:
1938:
1923:
1818:
1748:
1728:
1643:
1426:
1398:
1306:
1257:
1231:
985:
949:
914:
741:
723:
Advanced
Organic Chemistry: Reactions, Mechanisms, and Structure, 3rd edition
703:
624:) in the presence of strong base is a classic approach for the generation of
431:
301:
285:
165:
138:
60:
32:
1033:
881:
3743:
3103:
2855:
2632:
2232:
2032:
1883:
1878:
1743:
1598:
1378:
1184:
1091:
1081:
993:
848:
460:
452:
319:
209:
86:
24:
2242:
1888:
1858:
1623:
1337:
1272:
717:
491:
480:
393:
is the reaction of tert-butylbromide with potassium ethoxide in ethanol.
279:
48:
28:
941:
620:. For instance, α-elimination the elements of HCl from chloroform (CHCl
4526:
4053:
3403:
617:
275:
977:
840:
777:
1388:
546:
2 for strongly basic nucleophiles. Unhindered 1° haloalkanes favor S
337:
245:
71:
753:
1933:
1603:
589:
2 possible) on the other hand has a KIE of 0.85 consistent with a S
574:
233:
169:
75:
866:. Dougherty, Dennis A., 1952-. Sausalito, CA: University Science.
605:
1593:
1022:
597:
484:
443:
435:
365:
results from antiperiplanar elimination. The presence of product
345:
297:
alkyl halides, but is possible with some secondary alkyl halides.
241:
149:
79:
1010:
927:
439:
82:
179:. It must be strong enough to remove a weakly acidic hydrogen.
1291:
648:
tosylate has been used to prepare strained bicyclic systems.
356:
E1 elimination Nash 2008, antiperiplanar relationship in blue
962:
577:
ion. In accordance with an E2 elimination the reaction with
562:-butoxide). Similarly, attempts to effect substitution by S
467:. Generally, elimination is favored over substitution when
636:. (Confusingly, in organometallic terminology, the terms
336:
There is no antiperiplanar requirement. An example is the
1111:
333:
of slightly larger than 1 (commonly 1 - 1.5) is observed.
85:
proceed through an "internal" elimination mechanism, the
688:
Coleman, G. H.; Johnstone, H. F. (1925). "Cyclohexene".
451:. More precisely, there are competitions between E2 and
326:
because they share a common carbocationic intermediate.
897:
The organometallic chemistry of the transition metals
4668:
Erlenmeyer–Plöchl azlactone and amino-acid synthesis
805:(5th ed.). New York: McGraw-Hill. p. 350.
894:
369:
is an indication that an E1 mechanism is occurring.
3729:Divinylcyclopropane-cycloheptadiene rearrangement
421:Independent of concentration and basicity of base
4803:
687:
1522:
861:
425:
127:E2 is a single step elimination, with a single
3989:Thermal rearrangement of aromatic hydrocarbons
2623:Thermal rearrangement of aromatic hydrocarbons
598:Elimination reactions other than β-elimination
205:much larger than 1 (commonly 2-6) is observed.
123:The specifics of the reaction are as follows:
4718:Lectka enantioselective beta-lactam synthesis
1978:
1508:
1063:
1049:
55:, and the two-step mechanism is known as the
4497:Inverse electron-demand Diels–Alder reaction
2318:Heterogeneous metal catalyzed cross-coupling
716:
604:
182:In order for the pi bond to be created, the
3839:Lobry de Bruyn–Van Ekenstein transformation
278:: the carbon-halogen bond breaks to give a
1515:
1501:
1056:
1042:
4329:Petrenko-Kritschenko piperidone synthesis
3784:Fritsch–Buttenberg–Wiechell rearrangement
268:It is a two-step process of elimination:
105:, involves a one-step mechanism in which
4492:Intramolecular Diels–Alder cycloaddition
930:Journal of the American Chemical Society
18:
228:An example of this type of reaction in
4804:
4512:Metal-centered cycloaddition reactions
4164:Debus–Radziszewski imidazole synthesis
2108:Bodroux–Chichibabin aldehyde synthesis
1082:Unimolecular nucleophilic substitution
899:(5th ed.). Hoboken, N.J.: Wiley.
494:. Bases with steric bulk, (such as in
101:The E2 mechanism, where E2 stands for
4658:Diazoalkane 1,3-dipolar cycloaddition
4562:Vinylcyclopropane (5+2) cycloaddition
4467:Diazoalkane 1,3-dipolar cycloaddition
4239:Hurd–Mori 1,2,3-thiadiazole synthesis
3734:Dowd–Beckwith ring-expansion reaction
2901:Hurd–Mori 1,2,3-thiadiazole synthesis
1977:
1814:LFER solvent coefficients (data page)
1496:
1092:Bimolecular nucleophilic substitution
1037:
800:
318:E1 reactions are in competition with
264:and has the following specifications
3469:Sharpless asymmetric dihydroxylation
2706:Methoxymethylenetriphenylphosphorane
186:of carbons needs to be lowered from
3594:Allen–Millar–Trippett rearrangement
1145:Electrophilic aromatic substitution
434:is influenced by the reactivity of
374:It is accompanied by carbocationic
113:bonds break to form a double bond (
13:
4733:Nitrone-olefin (3+2) cycloaddition
4728:Niementowski quinazoline synthesis
4517:Nitrone-olefin (3+2) cycloaddition
4442:Azide-alkyne Huisgen cycloaddition
4304:Niementowski quinazoline synthesis
4059:Azide-alkyne Huisgen cycloaddition
3364:Meerwein–Ponndorf–Verley reduction
2916:Leimgruber–Batcho indole synthesis
1112:Nucleophilic internal substitution
1102:Nucleophilic aromatic substitution
380:
351:
219:
14:
4833:
4557:Trimethylenemethane cycloaddition
4259:Johnson–Corey–Chaykovsky reaction
4124:Cadogan–Sundberg indole synthesis
4104:Bohlmann–Rahtz pyridine synthesis
4064:Baeyer–Emmerling indole synthesis
2871:Cadogan–Sundberg indole synthesis
2363:Johnson–Corey–Chaykovsky reaction
1003:
864:Modern physical organic chemistry
4653:Cook–Heilbron thiazole synthesis
4482:Hexadehydro Diels–Alder reaction
4309:Niementowski quinoline synthesis
4139:Cook–Heilbron thiazole synthesis
4084:Bischler–Möhlau indole synthesis
3994:Tiffeneau–Demjanov rearrangement
3624:Baker–Venkataraman rearrangement
2782:Horner–Wadsworth–Emmons reaction
2453:Mizoroki-Heck vs. Reductive Heck
2338:Horner–Wadsworth–Emmons reaction
1849:Neighbouring group participation
1021:
1009:
197:The C-H bond is weakened in the
4189:Fiesselmann thiophene synthesis
4019:Westphalen–Lettré rearrangement
3999:Vinylcyclopropane rearrangement
3829:Kornblum–DeLaMare rearrangement
3474:Epoxidation of allylic alcohols
3384:Noyori asymmetric hydrogenation
3319:Kornblum–DeLaMare rearrangement
2994:Gallagher–Hollander degradation
1268:Lindemann–Hinshelwood mechanism
956:
498:), are often poor nucleophiles.
385:Scheme 2. E1 reaction mechanism
255:
224:Scheme 1: E2 reaction mechanism
96:
4648:Chichibabin pyridine synthesis
4134:Chichibabin pyridine synthesis
4094:Blum–Ittah aziridine synthesis
3929:Ring expansion and contraction
2198:Cross dehydrogenative coupling
1317:Outer sphere electron transfer
1312:Inner sphere electron transfer
1122:Nucleophilic acyl substitution
921:
888:
855:
819:
794:
784:
747:
710:
681:
474:around the α-carbon increases.
293:E1 typically takes place with
1:
4618:Bischler–Napieralski reaction
4576:Heterocycle forming reactions
4229:Hemetsberger indole synthesis
4089:Bischler–Napieralski reaction
4004:Wagner–Meerwein rearrangement
3974:Sommelet–Hauser rearrangement
3954:Seyferth–Gilbert homologation
3819:Ireland–Claisen rearrangement
3814:Hofmann–Martius rearrangement
3574:2,3-sigmatropic rearrangement
3189:Corey–Winter olefin synthesis
3114:Barton–McCombie deoxygenation
2757:Corey–Winter olefin synthesis
2711:Seyferth–Gilbert homologation
2578:Seyferth–Gilbert homologation
1482:Diffusion-controlled reaction
757:Journal of Chemical Education
675:
581:results in a KIE of 2.3. The
168:transition state which is in
4723:Lehmstedt–Tanasescu reaction
4683:Gabriel–Colman rearrangement
4638:Bucherer carbazole synthesis
4633:Borsche–Drechsel cyclization
4613:Bernthsen acridine synthesis
4598:Bamberger triazine synthesis
4583:Algar–Flynn–Oyamada reaction
4294:Nazarov cyclization reaction
4159:De Kimpe aziridine synthesis
4114:Bucherer carbazole synthesis
4109:Borsche–Drechsel cyclization
3879:Nazarov cyclization reaction
3859:Meyer–Schuster rearrangement
3789:Gabriel–Colman rearrangement
3539:Wolffenstein–Böters reaction
3424:Reduction of nitro compounds
3274:Grundmann aldehyde synthesis
3079:Algar–Flynn–Oyamada reaction
2488:Olefin conversion technology
2483:Nozaki–Hiyama–Kishi reaction
2278:Gabriel–Colman rearrangement
2168:Claisen-Schmidt condensation
2113:Bouveault aldehyde synthesis
895:Crabtree, Robert H. (2009).
426:Competition among mechanisms
270:ionization and deprotonation
244:. The reaction products are
63:, a third type of reaction,
7:
4698:Hantzsch pyridine synthesis
4477:Enone–alkene cycloadditions
4299:Nenitzescu indole synthesis
4219:Hantzsch pyridine synthesis
4184:Ferrario–Ackermann reaction
3834:Kowalski ester homologation
3799:Halogen dance rearrangement
3644:Benzilic acid rearrangement
3069:Akabori amino-acid reaction
3029:Von Braun amide degradation
2974:Barbier–Wieland degradation
2926:Nenitzescu indole synthesis
2906:Kharasch–Sosnovsky reaction
2797:Julia–Kocienski olefination
2701:Kowalski ester homologation
2398:Kowalski ester homologation
2373:Julia–Kocienski olefination
2128:Cadiot–Chodkiewicz coupling
2053:Aza-Baylis–Hillman reaction
1998:Acetoacetic ester synthesis
1709:Dynamic binding (chemistry)
1699:Conrotatory and disrotatory
1674:Charge remote fragmentation
1137:Electrophilic substitutions
663:
175:E2 typically uses a strong
10:
4840:
4763:Robinson–Gabriel synthesis
4713:Kröhnke pyridine synthesis
4547:Retro-Diels–Alder reaction
4487:Imine Diels–Alder reaction
4274:Kröhnke pyridine synthesis
3889:Newman–Kwart rearrangement
3864:Mislow–Evans rearrangement
3774:Fischer–Hepp rearrangement
3719:Di-Ď€-methane rearrangement
3499:Stephen aldehyde synthesis
3234:Eschweiler–Clarke reaction
2951:Williamson ether synthesis
2268:Fujiwara–Moritani reaction
2173:Combes quinoline synthesis
2138:Carbonyl olefin metathesis
1839:More O'Ferrall–Jencks plot
1764:Grunwald–Winstein equation
1734:Electron-withdrawing group
1669:Catalytic resonance theory
1447:Energy profile (chemistry)
1409:More O'Ferrall–Jencks plot
1074:Nucleophilic substitutions
801:Carey, Francis A. (2003).
651:
508:Williamson ether synthesis
414:Specific features :
4773:Urech hydantoin synthesis
4753:Pomeranz–Fritsch reaction
4678:Fischer oxazole synthesis
4575:
4412:1,3-Dipolar cycloaddition
4402:
4384:Urech hydantoin synthesis
4354:Reissert indole synthesis
4339:Pomeranz–Fritsch reaction
4269:Knorr quinoline synthesis
4199:Fischer oxazole synthesis
4129:Camps quinoline synthesis
4049:1,3-Dipolar cycloaddition
4037:
3949:Semipinacol rearrangement
3924:Ramberg–Bäcklund reaction
3909:Piancatelli rearrangement
3849:McFadyen–Stevens reaction
3604:Alpha-ketol rearrangement
3552:
3359:McFadyen–Stevens reaction
3304:Kiliani–Fischer synthesis
3224:Elbs persulfate oxidation
3149:Bouveault–Blanc reduction
3109:Baeyer–Villiger oxidation
3047:
2964:
2941:Schotten–Baumann reaction
2844:
2817:Ramberg–Bäcklund reaction
2724:
2696:Kiliani–Fischer synthesis
2676:
2538:Ramberg–Bäcklund reaction
2523:Pinacol coupling reaction
2518:Piancatelli rearrangement
2413:Liebeskind–Srogl coupling
2263:Fujimoto–Belleau reaction
1986:
1980:List of organic reactions
1844:Negative hyperconjugation
1589:
1531:
1477:Michaelis–Menten kinetics
1417:
1351:
1325:
1281:
1245:
1197:
1158:
1135:
1072:
670:E1cB-elimination reaction
449:nucleophilic substitution
164:with lower energy than a
70:, exists. Finally, the
4748:Pictet–Spengler reaction
4663:Einhorn–Brunner reaction
4628:Boger pyridine synthesis
4522:Oxo-Diels–Alder reaction
4437:Aza-Diels–Alder reaction
4334:Pictet–Spengler reaction
4234:Hofmann–Löffler reaction
4224:Hegedus indole synthesis
4194:Fischer indole synthesis
4069:Bartoli indole synthesis
4024:Willgerodt rearrangement
3854:McLafferty rearrangement
3764:Ferrier carbocyclization
3579:2,3-Wittig rearrangement
3569:1,2-Wittig rearrangement
3409:Parikh–Doering oxidation
3399:Oxygen rebound mechanism
3064:Adkins–Peterson reaction
2956:Yamaguchi esterification
2896:Hegedus indole synthesis
2861:Bartoli indole synthesis
2732:Bamford–Stevens reaction
2648:Weinreb ketone synthesis
2608:Stork enamine alkylation
2383:Knoevenagel condensation
2253:Ferrier carbocyclization
2143:Castro–Stephens coupling
1769:Hammett acidity function
1759:Free-energy relationship
1704:Curtin–Hammett principle
1689:Conformational isomerism
1404:Potential energy surface
1283:Electron/Proton transfer
1168:Unimolecular elimination
862:Anslyn, Eric V. (2006).
704:10.15227/orgsyn.005.0033
477:a stronger base is used.
459:and also between E1 and
331:deuterium isotope effect
262:unimolecular elimination
203:deuterium isotope effect
201:and therefore a primary
23:Elimination reaction of
4708:Knorr pyrrole synthesis
4643:Bucherer–Bergs reaction
4588:Allan–Robinson reaction
4567:Wagner-Jauregg reaction
4359:Ring-closing metathesis
4284:Larock indole synthesis
4264:Knorr pyrrole synthesis
4119:Bucherer–Bergs reaction
3984:Stieglitz rearrangement
3964:Skattebøl rearrangement
3934:Ring-closing metathesis
3794:Group transfer reaction
3759:Favorskii rearrangement
3699:Cornforth rearrangement
3629:Bamberger rearrangement
3534:Wolff–Kishner reduction
3354:Markó–Lam deoxygenation
3249:Fleming–Tamao oxidation
3244:Fischer–Tropsch process
2931:Oxymercuration reaction
2911:Knorr pyrrole synthesis
2737:Barton–Kellogg reaction
2643:Wagner-Jauregg reaction
2563:Ring-closing metathesis
2553:Reimer–Tiemann reaction
2543:Rauhut–Currier reaction
2458:Nef isocyanide reaction
2418:Malonic ester synthesis
2388:Knorr pyrrole synthesis
2323:High dilution principle
2258:Friedel–Crafts reaction
2193:Cross-coupling reaction
2118:Bucherer–Bergs reaction
2103:Blanc chloromethylation
2093:Blaise ketone synthesis
2068:Baylis–Hillman reaction
2063:Barton–Kellogg reaction
2038:Allan–Robinson reaction
1944:Woodward–Hoffmann rules
1679:Charge-transfer complex
1452:Transition state theory
1253:Intramolecular reaction
1179:Bimolecular elimination
658:Christopher Kelk Ingold
521:1 and E1 pathways.
496:potassium tert-butoxide
376:rearrangement reactions
103:bimolecular elimination
4673:Feist–Benary synthesis
4447:Bradsher cycloaddition
4417:4+4 Photocycloaddition
4374:Simmons–Smith reaction
4319:Paternò–Büchi reaction
4179:Feist–Benary synthesis
4169:Dieckmann condensation
3919:Pummerer rearrangement
3899:Oxy-Cope rearrangement
3874:Myers allene synthesis
3824:Jacobsen rearrangement
3739:Electrocyclic reaction
3714:Demjanov rearrangement
3669:Buchner ring expansion
3639:Beckmann rearrangement
3619:Aza-Cope rearrangement
3614:Arndt–Eistert reaction
3589:Alkyne zipper reaction
3509:Transfer hydrogenation
3484:Sharpless oxyamination
3459:Selenoxide elimination
3344:Lombardo methylenation
3269:Griesbaum coozonolysis
3179:Corey–Itsuno reduction
3154:Boyland–Sims oxidation
3094:Angeli–Rimini reaction
2742:Boord olefin synthesis
2686:Arndt–Eistert reaction
2678:Homologation reactions
2478:Nitro-Mannich reaction
2393:Kolbe–Schmitt reaction
2203:Cross-coupling partner
2123:Buchner ring expansion
2043:Arndt–Eistert reaction
1809:Kinetic isotope effect
1556:Rearrangement reaction
1246:Unimolecular reactions
1207:Electrophilic addition
1026:Quotations related to
609:
571:kinetic isotope effect
418:Rearrangement possible
386:
361:Only reaction product
357:
225:
162:staggered conformation
36:
4817:Olefination reactions
4812:Elimination reactions
4532:Pauson–Khand reaction
4369:Sharpless epoxidation
4324:Pechmann condensation
4204:Friedländer synthesis
4154:Davis–Beirut reaction
4009:Wallach rearrangement
3979:Stevens rearrangement
3914:Pinacol rearrangement
3894:Overman rearrangement
3809:Hofmann rearrangement
3804:Hayashi rearrangement
3769:Ferrier rearrangement
3724:Dimroth rearrangement
3709:Curtius rearrangement
3704:Criegee rearrangement
3684:Claisen rearrangement
3674:Carroll rearrangement
3609:Amadori rearrangement
3599:Allylic rearrangement
3479:Sharpless epoxidation
3214:Dess–Martin oxidation
3139:Bohn–Schmidt reaction
2999:Hofmann rearrangement
2802:Kauffmann olefination
2725:Olefination reactions
2663:Wurtz–Fittig reaction
2498:Palladium–NHC complex
2378:Kauffmann olefination
2333:Homologation reaction
2183:Corey–House synthesis
2163:Claisen rearrangement
1959:Yukawa–Tsuno equation
1919:Swain–Lupton equation
1899:Spherical aromaticity
1834:Möbius–Hückel concept
1619:Aromatic ring current
1581:Substitution reaction
1437:Rate-determining step
1369:Reactive intermediate
1227:Free-radical addition
1217:Nucleophilic addition
1160:Elimination reactions
1016:Elimination reactions
634:reductive elimination
608:
384:
355:
312:apply (unimolecular).
306:rate-determining step
223:
208:E2 competes with the
199:rate determining step
22:
4738:Paal–Knorr synthesis
4608:Barton–Zard reaction
4552:Staudinger synthesis
4502:Ketene cycloaddition
4472:Diels–Alder reaction
4452:Cheletropic reaction
4432:Alkyne trimerisation
4314:Paal–Knorr synthesis
4279:Kulinkovich reaction
4254:Jacobsen epoxidation
4174:Diels–Alder reaction
3969:Smiles rearrangement
3959:Sigmatropic reaction
3844:Lossen rearrangement
3694:Corey–Fuchs reaction
3659:Boekelheide reaction
3654:Bergmann degradation
3584:Achmatowicz reaction
3369:Methionine sulfoxide
3169:Clemmensen reduction
3129:Bergmann degradation
3059:Acyloin condensation
3024:Strecker degradation
2979:Bergmann degradation
2946:Ullmann condensation
2812:Peterson olefination
2787:Hydrazone iodination
2767:Elimination reaction
2668:Zincke–Suhl reaction
2588:Sonogashira coupling
2548:Reformatsky reaction
2508:Peterson olefination
2473:Nierenstein reaction
2403:Kulinkovich reaction
2218:Diels–Alder reaction
2178:Corey–Fuchs reaction
2158:Claisen condensation
2028:Alkyne trimerisation
2003:Acyloin condensation
1969:ÎŁ-bishomoaromaticity
1929:Thorpe–Ingold effect
1541:Elimination reaction
1432:Equilibrium constant
1028:Elimination reaction
1018:at Wikimedia Commons
483:increases (increase
310:first-order kinetics
156:. An antiperiplanar
41:elimination reaction
4822:Reaction mechanisms
4758:Prilezhaev reaction
4743:Pellizzari reaction
4422:(4+3) cycloaddition
4389:Van Leusen reaction
4364:Robinson annulation
4349:Pschorr cyclization
4344:Prilezhaev reaction
4074:Bergman cyclization
4029:Wolff rearrangement
4014:Weerman degradation
3904:Pericyclic reaction
3884:Neber rearrangement
3779:Fries rearrangement
3664:Brook rearrangement
3649:Bergman cyclization
3494:Staudinger reaction
3439:Rosenmund reduction
3429:Reductive amination
3394:Oppenauer oxidation
3184:Corey–Kim oxidation
3159:Cannizzaro reaction
3034:Weerman degradation
3009:Isosaccharinic acid
2921:Mukaiyama hydration
2777:Hofmann elimination
2762:Dehydrohalogenation
2747:Chugaev elimination
2568:Robinson annulation
2513:Pfitzinger reaction
2283:Gattermann reaction
2228:Wulff–Dötz reaction
2208:Dakin–West reaction
2133:Carbonyl allylation
2078:Bergman cyclization
1864:Kennedy J. P. Orton
1784:Hammond's postulate
1754:Flippin–Lodge angle
1724:Electromeric effect
1649:Beta-silicon effect
1634:Baker–Nathan effect
1442:Reaction coordinate
1374:Radical (chemistry)
1359:Elementary reaction
1302:Grotthuss mechanism
1066:reaction mechanisms
942:10.1021/ja00394a043
770:2008JChEd..85..552N
726:, New York: Wiley,
490:the base is a poor
288:of the carbocation.
232:is the reaction of
4507:McCormack reaction
4457:Conia-ene reaction
4289:Madelung synthesis
4079:Biginelli reaction
3869:Mumm rearrangement
3754:Favorskii reaction
3689:Cope rearrangement
3679:Chan rearrangement
3444:Rubottom oxidation
3374:Miyaura borylation
3339:Lipid peroxidation
3334:Lindgren oxidation
3314:Kornblum oxidation
3309:Kolbe electrolysis
3254:Fukuyama reduction
3164:Carbonyl reduction
3014:Marker degradation
2876:Diazonium compound
2866:Boudouard reaction
2845:Carbon-heteroatom
2772:Grieco elimination
2558:Rieche formylation
2503:Passerini reaction
2433:Meerwein arylation
2353:Hydroxymethylation
2248:Favorskii reaction
2148:Chan rearrangement
2083:Biginelli reaction
2008:Aldol condensation
1854:2-Norbornyl cation
1829:Möbius aromaticity
1824:Markovnikov's rule
1719:Effective molarity
1664:Bürgi–Dunitz angle
1654:Bicycloaromaticity
1467:Arrhenius equation
1237:Oxidative addition
1199:Addition reactions
610:
387:
358:
238:potassium ethoxide
226:
37:
4799:
4798:
4795:
4794:
4791:
4790:
4783:Wohl–Aue reaction
4427:6+4 Cycloaddition
4244:Iodolactonization
3564:1,2-rearrangement
3529:Wohl–Aue reaction
3449:Sabatier reaction
3414:Pinnick oxidation
3379:Mozingo reduction
3324:Leuckart reaction
3279:Haloform reaction
3194:Criegee oxidation
3174:Collins oxidation
3124:Benkeser reaction
3119:Bechamp reduction
3089:Andrussow process
3074:Alcohol oxidation
2984:Edman degradation
2891:Haloform reaction
2840:
2839:
2827:Takai olefination
2792:Julia olefination
2618:Takai olefination
2493:Olefin metathesis
2368:Julia olefination
2293:Grignard reaction
2273:Fukuyama coupling
2188:Coupling reaction
2153:Chan–Lam coupling
2023:Alkyne metathesis
2018:Alkane metathesis
1874:Phosphaethynolate
1779:George S. Hammond
1739:Electronic effect
1694:Conjugated system
1576:Stereospecificity
1571:Stereoselectivity
1536:Addition reaction
1525:organic reactions
1490:
1489:
1462:Activated complex
1457:Activation energy
1419:Chemical kinetics
1364:Reaction dynamics
1263:Photodissociation
1014:Media related to
978:10.1021/ol200121f
841:10.1021/ja057491d
829:J. Am. Chem. Soc.
803:Organic Chemistry
778:10.1021/ed085p552
691:Organic Syntheses
569:In one study the
250:potassium bromide
4829:
4778:Wenker synthesis
4768:Stollé synthesis
4623:Bobbitt reaction
4593:Auwers synthesis
4537:Povarov reaction
4462:Cyclopropanation
4400:
4399:
4394:Wenker synthesis
4149:Darzens reaction
4099:Bobbitt reaction
3944:Schmidt reaction
3749:Enyne metathesis
3524:Whiting reaction
3519:Wharton reaction
3464:Shapiro reaction
3454:Sarett oxidation
3419:Prévost reaction
3229:Emde degradation
3039:Wohl degradation
3019:Ruff degradation
2989:Emde degradation
2886:Grignard reagent
2822:Shapiro reaction
2807:McMurry reaction
2674:
2673:
2638:Ullmann reaction
2603:Stollé synthesis
2593:Stetter reaction
2583:Shapiro reaction
2573:Sakurai reaction
2468:Negishi coupling
2448:Minisci reaction
2443:Michael reaction
2428:McMurry reaction
2423:Mannich reaction
2303:Hammick reaction
2298:Grignard reagent
2238:Enyne metathesis
2223:Doebner reaction
2213:Darzens reaction
2058:Barbier reaction
2048:Auwers synthesis
1975:
1974:
1949:Woodward's rules
1914:Superaromaticity
1904:Spiroaromaticity
1804:Inductive effect
1799:Hyperconjugation
1774:Hammett equation
1714:Edwards equation
1566:Regioselectivity
1517:
1510:
1503:
1494:
1493:
1394:Collision theory
1343:Matrix isolation
1297:Harpoon reaction
1174:E1cB-elimination
1058:
1051:
1044:
1035:
1034:
1025:
1013:
998:
997:
972:(7): 1646–1649.
960:
954:
953:
925:
919:
918:
892:
886:
885:
859:
853:
852:
823:
817:
816:
798:
792:
788:
782:
781:
751:
745:
744:
714:
708:
707:
685:
585:reaction (only S
579:t-butyl chloride
472:steric hindrance
158:transition state
129:transition state
45:organic reaction
4839:
4838:
4832:
4831:
4830:
4828:
4827:
4826:
4802:
4801:
4800:
4787:
4688:Gewald reaction
4571:
4398:
4379:Skraup reaction
4214:Graham reaction
4209:Gewald reaction
4040:
4033:
3555:
3548:
3504:Swern oxidation
3489:Stahl oxidation
3434:Riley oxidation
3389:Omega oxidation
3349:Luche reduction
3299:Jones oxidation
3264:Glycol cleavage
3259:Ganem oxidation
3204:Davis oxidation
3199:Dakin oxidation
3134:Birch reduction
3084:Amide reduction
3050:
3043:
3004:Hooker reaction
2966:
2960:
2848:
2846:
2836:
2832:Wittig reaction
2720:
2716:Wittig reaction
2691:Hooker reaction
2672:
2653:Wittig reaction
2628:Thorpe reaction
2613:Suzuki reaction
2598:Stille reaction
2533:Quelet reaction
2408:Kumada coupling
2358:Ivanov reaction
2348:Hydrovinylation
2328:Hiyama coupling
2288:Glaser coupling
2098:Blaise reaction
2088:Bingel reaction
2073:Benary reaction
1990:
1988:
1982:
1973:
1869:Passive binding
1789:Homoaromaticity
1639:Baldwin's rules
1614:Antiaromaticity
1609:Anomeric effect
1585:
1527:
1521:
1491:
1486:
1472:Eyring equation
1413:
1384:Stereochemistry
1347:
1333:Solvent effects
1321:
1277:
1241:
1222:
1212:
1193:
1188:
1154:
1150:
1131:
1127:
1117:
1107:
1097:
1087:
1068:
1062:
1006:
1001:
966:Organic Letters
961:
957:
926:
922:
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874:
860:
856:
824:
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813:
799:
795:
789:
785:
752:
748:
734:
715:
711:
686:
682:
678:
666:
654:
631:
626:dichlorocarbene
623:
614:carbon monoxide
600:
592:
588:
583:methyl chloride
565:
556:
549:
545:
538:
534:
530:
520:
513:
505:
464:
456:
428:
410:
342:sulfonate ester
323:
258:
234:isobutylbromide
213:
107:carbon-hydrogen
99:
90:
68:
17:
12:
11:
5:
4837:
4836:
4825:
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4819:
4814:
4797:
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4788:
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4745:
4740:
4735:
4730:
4725:
4720:
4715:
4710:
4705:
4700:
4695:
4693:Hantzsch ester
4690:
4685:
4680:
4675:
4670:
4665:
4660:
4655:
4650:
4645:
4640:
4635:
4630:
4625:
4620:
4615:
4610:
4605:
4603:Banert cascade
4600:
4595:
4590:
4585:
4579:
4577:
4573:
4572:
4570:
4569:
4564:
4559:
4554:
4549:
4544:
4542:Prato reaction
4539:
4534:
4529:
4524:
4519:
4514:
4509:
4504:
4499:
4494:
4489:
4484:
4479:
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4464:
4459:
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3696:
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3676:
3671:
3666:
3661:
3656:
3651:
3646:
3641:
3636:
3634:Banert cascade
3631:
3626:
3621:
3616:
3611:
3606:
3601:
3596:
3591:
3586:
3581:
3576:
3571:
3566:
3560:
3558:
3554:Rearrangement
3550:
3549:
3547:
3546:
3544:Zinin reaction
3541:
3536:
3531:
3526:
3521:
3516:
3514:Wacker process
3511:
3506:
3501:
3496:
3491:
3486:
3481:
3476:
3471:
3466:
3461:
3456:
3451:
3446:
3441:
3436:
3431:
3426:
3421:
3416:
3411:
3406:
3401:
3396:
3391:
3386:
3381:
3376:
3371:
3366:
3361:
3356:
3351:
3346:
3341:
3336:
3331:
3326:
3321:
3316:
3311:
3306:
3301:
3296:
3291:
3289:Hydrogenolysis
3286:
3281:
3276:
3271:
3266:
3261:
3256:
3251:
3246:
3241:
3239:Étard reaction
3236:
3231:
3226:
3221:
3216:
3211:
3206:
3201:
3196:
3191:
3186:
3181:
3176:
3171:
3166:
3161:
3156:
3151:
3146:
3144:Bosch reaction
3141:
3136:
3131:
3126:
3121:
3116:
3111:
3106:
3101:
3096:
3091:
3086:
3081:
3076:
3071:
3066:
3061:
3055:
3053:
3049:Organic redox
3045:
3044:
3042:
3041:
3036:
3031:
3026:
3021:
3016:
3011:
3006:
3001:
2996:
2991:
2986:
2981:
2976:
2970:
2968:
2962:
2961:
2959:
2958:
2953:
2948:
2943:
2938:
2933:
2928:
2923:
2918:
2913:
2908:
2903:
2898:
2893:
2888:
2883:
2881:Esterification
2878:
2873:
2868:
2863:
2858:
2852:
2850:
2842:
2841:
2838:
2837:
2835:
2834:
2829:
2824:
2819:
2814:
2809:
2804:
2799:
2794:
2789:
2784:
2779:
2774:
2769:
2764:
2759:
2754:
2749:
2744:
2739:
2734:
2728:
2726:
2722:
2721:
2719:
2718:
2713:
2708:
2703:
2698:
2693:
2688:
2682:
2680:
2671:
2670:
2665:
2660:
2658:Wurtz reaction
2655:
2650:
2645:
2640:
2635:
2630:
2625:
2620:
2615:
2610:
2605:
2600:
2595:
2590:
2585:
2580:
2575:
2570:
2565:
2560:
2555:
2550:
2545:
2540:
2535:
2530:
2528:Prins reaction
2525:
2520:
2515:
2510:
2505:
2500:
2495:
2490:
2485:
2480:
2475:
2470:
2465:
2460:
2455:
2450:
2445:
2440:
2435:
2430:
2425:
2420:
2415:
2410:
2405:
2400:
2395:
2390:
2385:
2380:
2375:
2370:
2365:
2360:
2355:
2350:
2345:
2343:Hydrocyanation
2340:
2335:
2330:
2325:
2320:
2315:
2313:Henry reaction
2310:
2305:
2300:
2295:
2290:
2285:
2280:
2275:
2270:
2265:
2260:
2255:
2250:
2245:
2240:
2235:
2230:
2225:
2220:
2215:
2210:
2205:
2200:
2195:
2190:
2185:
2180:
2175:
2170:
2165:
2160:
2155:
2150:
2145:
2140:
2135:
2130:
2125:
2120:
2115:
2110:
2105:
2100:
2095:
2090:
2085:
2080:
2075:
2070:
2065:
2060:
2055:
2050:
2045:
2040:
2035:
2030:
2025:
2020:
2015:
2013:Aldol reaction
2010:
2005:
2000:
1994:
1992:
1987:Carbon-carbon
1984:
1983:
1972:
1971:
1966:
1964:Zaitsev's rule
1961:
1956:
1951:
1946:
1941:
1936:
1931:
1926:
1921:
1916:
1911:
1909:Steric effects
1906:
1901:
1896:
1891:
1886:
1881:
1876:
1871:
1866:
1861:
1856:
1851:
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:
1590:
1587:
1586:
1584:
1583:
1578:
1573:
1568:
1563:
1561:Redox reaction
1558:
1553:
1548:
1546:Polymerization
1543:
1538:
1532:
1529:
1528:
1520:
1519:
1512:
1505:
1497:
1488:
1487:
1485:
1484:
1479:
1474:
1469:
1464:
1459:
1454:
1449:
1444:
1439:
1434:
1429:
1423:
1421:
1415:
1414:
1412:
1411:
1406:
1401:
1396:
1391:
1386:
1381:
1376:
1371:
1366:
1361:
1355:
1353:
1352:Related topics
1349:
1348:
1346:
1345:
1340:
1335:
1329:
1327:
1326:Medium effects
1323:
1322:
1320:
1319:
1314:
1309:
1304:
1299:
1294:
1288:
1286:
1279:
1278:
1276:
1275:
1270:
1265:
1260:
1255:
1249:
1247:
1243:
1242:
1240:
1239:
1234:
1229:
1224:
1220:
1214:
1210:
1203:
1201:
1195:
1194:
1192:
1191:
1186:
1182:
1176:
1171:
1164:
1162:
1156:
1155:
1153:
1152:
1148:
1141:
1139:
1133:
1132:
1130:
1129:
1125:
1119:
1115:
1109:
1105:
1099:
1095:
1089:
1085:
1078:
1076:
1070:
1069:
1061:
1060:
1053:
1046:
1038:
1032:
1031:
1019:
1005:
1004:External links
1002:
1000:
999:
955:
936:(4): 948–949.
920:
905:
887:
872:
854:
835:(3): 736–737.
818:
811:
793:
783:
746:
732:
709:
679:
677:
674:
673:
672:
665:
662:
660:in the 1920s.
653:
650:
629:
621:
599:
596:
590:
586:
563:
554:
547:
543:
536:
532:
528:
518:
511:
503:
500:
499:
488:
478:
475:
462:
454:
427:
424:
423:
422:
419:
408:
405:
404:
401:
389:An example in
379:
378:
371:
370:
350:
349:
334:
327:
321:
316:
313:
298:
291:
290:
289:
283:
257:
254:
248:, ethanol and
218:
217:
211:
206:
195:
180:
173:
154:antiperiplanar
146:
135:
132:
111:carbon-halogen
98:
95:
88:
66:
15:
9:
6:
4:
3:
2:
4835:
4834:
4823:
4820:
4818:
4815:
4813:
4810:
4809:
4807:
4784:
4781:
4779:
4776:
4774:
4771:
4769:
4766:
4764:
4761:
4759:
4756:
4754:
4751:
4749:
4746:
4744:
4741:
4739:
4736:
4734:
4731:
4729:
4726:
4724:
4721:
4719:
4716:
4714:
4711:
4709:
4706:
4704:
4703:Herz reaction
4701:
4699:
4696:
4694:
4691:
4689:
4686:
4684:
4681:
4679:
4676:
4674:
4671:
4669:
4666:
4664:
4661:
4659:
4656:
4654:
4651:
4649:
4646:
4644:
4641:
4639:
4636:
4634:
4631:
4629:
4626:
4624:
4621:
4619:
4616:
4614:
4611:
4609:
4606:
4604:
4601:
4599:
4596:
4594:
4591:
4589:
4586:
4584:
4581:
4580:
4578:
4574:
4568:
4565:
4563:
4560:
4558:
4555:
4553:
4550:
4548:
4545:
4543:
4540:
4538:
4535:
4533:
4530:
4528:
4525:
4523:
4520:
4518:
4515:
4513:
4510:
4508:
4505:
4503:
4500:
4498:
4495:
4493:
4490:
4488:
4485:
4483:
4480:
4478:
4475:
4473:
4470:
4468:
4465:
4463:
4460:
4458:
4455:
4453:
4450:
4448:
4445:
4443:
4440:
4438:
4435:
4433:
4430:
4428:
4425:
4423:
4420:
4418:
4415:
4413:
4410:
4409:
4407:
4405:
4404:Cycloaddition
4401:
4395:
4392:
4390:
4387:
4385:
4382:
4380:
4377:
4375:
4372:
4370:
4367:
4365:
4362:
4360:
4357:
4355:
4352:
4350:
4347:
4345:
4342:
4340:
4337:
4335:
4332:
4330:
4327:
4325:
4322:
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:
4249:Isay reaction
4247:
4245:
4242:
4240:
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:
4144:Cycloaddition
4142:
4140:
4137:
4135:
4132:
4130:
4127:
4125:
4122:
4120:
4117:
4115:
4112:
4110:
4107:
4105:
4102:
4100:
4097:
4095:
4092:
4090:
4087:
4085:
4082:
4080:
4077:
4075:
4072:
4070:
4067:
4065:
4062:
4060:
4057:
4055:
4052:
4050:
4047:
4046:
4044:
4042:
4039:Ring forming
4036:
4030:
4027:
4025:
4022:
4020:
4017:
4015:
4012:
4010:
4007:
4005:
4002:
4000:
3997:
3995:
3992:
3990:
3987:
3985:
3982:
3980:
3977:
3975:
3972:
3970:
3967:
3965:
3962:
3960:
3957:
3955:
3952:
3950:
3947:
3945:
3942:
3940:
3939:Rupe reaction
3937:
3935:
3932:
3930:
3927:
3925:
3922:
3920:
3917:
3915:
3912:
3910:
3907:
3905:
3902:
3900:
3897:
3895:
3892:
3890:
3887:
3885:
3882:
3880:
3877:
3875:
3872:
3870:
3867:
3865:
3862:
3860:
3857:
3855:
3852:
3850:
3847:
3845:
3842:
3840:
3837:
3835:
3832:
3830:
3827:
3825:
3822:
3820:
3817:
3815:
3812:
3810:
3807:
3805:
3802:
3800:
3797:
3795:
3792:
3790:
3787:
3785:
3782:
3780:
3777:
3775:
3772:
3770:
3767:
3765:
3762:
3760:
3757:
3755:
3752:
3750:
3747:
3745:
3742:
3740:
3737:
3735:
3732:
3730:
3727:
3725:
3722:
3720:
3717:
3715:
3712:
3710:
3707:
3705:
3702:
3700:
3697:
3695:
3692:
3690:
3687:
3685:
3682:
3680:
3677:
3675:
3672:
3670:
3667:
3665:
3662:
3660:
3657:
3655:
3652:
3650:
3647:
3645:
3642:
3640:
3637:
3635:
3632:
3630:
3627:
3625:
3622:
3620:
3617:
3615:
3612:
3610:
3607:
3605:
3602:
3600:
3597:
3595:
3592:
3590:
3587:
3585:
3582:
3580:
3577:
3575:
3572:
3570:
3567:
3565:
3562:
3561:
3559:
3557:
3551:
3545:
3542:
3540:
3537:
3535:
3532:
3530:
3527:
3525:
3522:
3520:
3517:
3515:
3512:
3510:
3507:
3505:
3502:
3500:
3497:
3495:
3492:
3490:
3487:
3485:
3482:
3480:
3477:
3475:
3472:
3470:
3467:
3465:
3462:
3460:
3457:
3455:
3452:
3450:
3447:
3445:
3442:
3440:
3437:
3435:
3432:
3430:
3427:
3425:
3422:
3420:
3417:
3415:
3412:
3410:
3407:
3405:
3402:
3400:
3397:
3395:
3392:
3390:
3387:
3385:
3382:
3380:
3377:
3375:
3372:
3370:
3367:
3365:
3362:
3360:
3357:
3355:
3352:
3350:
3347:
3345:
3342:
3340:
3337:
3335:
3332:
3330:
3329:Ley oxidation
3327:
3325:
3322:
3320:
3317:
3315:
3312:
3310:
3307:
3305:
3302:
3300:
3297:
3295:
3294:Hydroxylation
3292:
3290:
3287:
3285:
3284:Hydrogenation
3282:
3280:
3277:
3275:
3272:
3270:
3267:
3265:
3262:
3260:
3257:
3255:
3252:
3250:
3247:
3245:
3242:
3240:
3237:
3235:
3232:
3230:
3227:
3225:
3222:
3220:
3219:DNA oxidation
3217:
3215:
3212:
3210:
3209:Deoxygenation
3207:
3205:
3202:
3200:
3197:
3195:
3192:
3190:
3187:
3185:
3182:
3180:
3177:
3175:
3172:
3170:
3167:
3165:
3162:
3160:
3157:
3155:
3152:
3150:
3147:
3145:
3142:
3140:
3137:
3135:
3132:
3130:
3127:
3125:
3122:
3120:
3117:
3115:
3112:
3110:
3107:
3105:
3102:
3100:
3099:Aromatization
3097:
3095:
3092:
3090:
3087:
3085:
3082:
3080:
3077:
3075:
3072:
3070:
3067:
3065:
3062:
3060:
3057:
3056:
3054:
3052:
3046:
3040:
3037:
3035:
3032:
3030:
3027:
3025:
3022:
3020:
3017:
3015:
3012:
3010:
3007:
3005:
3002:
3000:
2997:
2995:
2992:
2990:
2987:
2985:
2982:
2980:
2977:
2975:
2972:
2971:
2969:
2963:
2957:
2954:
2952:
2949:
2947:
2944:
2942:
2939:
2937:
2936:Reed reaction
2934:
2932:
2929:
2927:
2924:
2922:
2919:
2917:
2914:
2912:
2909:
2907:
2904:
2902:
2899:
2897:
2894:
2892:
2889:
2887:
2884:
2882:
2879:
2877:
2874:
2872:
2869:
2867:
2864:
2862:
2859:
2857:
2854:
2853:
2851:
2847:bond forming
2843:
2833:
2830:
2828:
2825:
2823:
2820:
2818:
2815:
2813:
2810:
2808:
2805:
2803:
2800:
2798:
2795:
2793:
2790:
2788:
2785:
2783:
2780:
2778:
2775:
2773:
2770:
2768:
2765:
2763:
2760:
2758:
2755:
2753:
2752:Cope reaction
2750:
2748:
2745:
2743:
2740:
2738:
2735:
2733:
2730:
2729:
2727:
2723:
2717:
2714:
2712:
2709:
2707:
2704:
2702:
2699:
2697:
2694:
2692:
2689:
2687:
2684:
2683:
2681:
2679:
2675:
2669:
2666:
2664:
2661:
2659:
2656:
2654:
2651:
2649:
2646:
2644:
2641:
2639:
2636:
2634:
2631:
2629:
2626:
2624:
2621:
2619:
2616:
2614:
2611:
2609:
2606:
2604:
2601:
2599:
2596:
2594:
2591:
2589:
2586:
2584:
2581:
2579:
2576:
2574:
2571:
2569:
2566:
2564:
2561:
2559:
2556:
2554:
2551:
2549:
2546:
2544:
2541:
2539:
2536:
2534:
2531:
2529:
2526:
2524:
2521:
2519:
2516:
2514:
2511:
2509:
2506:
2504:
2501:
2499:
2496:
2494:
2491:
2489:
2486:
2484:
2481:
2479:
2476:
2474:
2471:
2469:
2466:
2464:
2463:Nef synthesis
2461:
2459:
2456:
2454:
2451:
2449:
2446:
2444:
2441:
2439:
2438:Methylenation
2436:
2434:
2431:
2429:
2426:
2424:
2421:
2419:
2416:
2414:
2411:
2409:
2406:
2404:
2401:
2399:
2396:
2394:
2391:
2389:
2386:
2384:
2381:
2379:
2376:
2374:
2371:
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:
2308:Heck reaction
2306:
2304:
2301:
2299:
2296:
2294:
2291:
2289:
2286:
2284:
2281:
2279:
2276:
2274:
2271:
2269:
2266:
2264:
2261:
2259:
2256:
2254:
2251:
2249:
2246:
2244:
2241:
2239:
2236:
2234:
2231:
2229:
2226:
2224:
2221:
2219:
2216:
2214:
2211:
2209:
2206:
2204:
2201:
2199:
2196:
2194:
2191:
2189:
2186:
2184:
2181:
2179:
2176:
2174:
2171:
2169:
2166:
2164:
2161:
2159:
2156:
2154:
2151:
2149:
2146:
2144:
2141:
2139:
2136:
2134:
2131:
2129:
2126:
2124:
2121:
2119:
2116:
2114:
2111:
2109:
2106:
2104:
2101:
2099:
2096:
2094:
2091:
2089:
2086:
2084:
2081:
2079:
2076:
2074:
2071:
2069:
2066:
2064:
2061:
2059:
2056:
2054:
2051:
2049:
2046:
2044:
2041:
2039:
2036:
2034:
2031:
2029:
2026:
2024:
2021:
2019:
2016:
2014:
2011:
2009:
2006:
2004:
2001:
1999:
1996:
1995:
1993:
1989:bond forming
1985:
1981:
1976:
1970:
1967:
1965:
1962:
1960:
1957:
1955:
1954:Y-aromaticity
1952:
1950:
1947:
1945:
1942:
1940:
1939:Walsh diagram
1937:
1935:
1932:
1930:
1927:
1925:
1924:Taft equation
1922:
1920:
1917:
1915:
1912:
1910:
1907:
1905:
1902:
1900:
1897:
1895:
1894:ÎŁ-aromaticity
1892:
1890:
1887:
1885:
1882:
1880:
1877:
1875:
1872:
1870:
1867:
1865:
1862:
1860:
1857:
1855:
1852:
1850:
1847:
1845:
1842:
1840:
1837:
1835:
1832:
1830:
1827:
1825:
1822:
1820:
1819:Marcus theory
1817:
1815:
1812:
1810:
1807:
1805:
1802:
1800:
1797:
1795:
1794:HĂĽckel's rule
1792:
1790:
1787:
1785:
1782:
1780:
1777:
1775:
1772:
1770:
1767:
1765:
1762:
1760:
1757:
1755:
1752:
1750:
1749:Evelyn effect
1747:
1745:
1742:
1740:
1737:
1735:
1732:
1730:
1729:Electron-rich
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:
1644:Bema Hapothle
1642:
1640:
1637:
1635:
1632:
1630:
1627:
1625:
1622:
1620:
1617:
1615:
1612:
1610:
1607:
1605:
1602:
1600:
1597:
1595:
1592:
1591:
1588:
1582:
1579:
1577:
1574:
1572:
1569:
1567:
1564:
1562:
1559:
1557:
1554:
1552:
1549:
1547:
1544:
1542:
1539:
1537:
1534:
1533:
1530:
1526:
1518:
1513:
1511:
1506:
1504:
1499:
1498:
1495:
1483:
1480:
1478:
1475:
1473:
1470:
1468:
1465:
1463:
1460:
1458:
1455:
1453:
1450:
1448:
1445:
1443:
1440:
1438:
1435:
1433:
1430:
1428:
1427:Rate equation
1425:
1424:
1422:
1420:
1416:
1410:
1407:
1405:
1402:
1400:
1399:Arrow pushing
1397:
1395:
1392:
1390:
1387:
1385:
1382:
1380:
1377:
1375:
1372:
1370:
1367:
1365:
1362:
1360:
1357:
1356:
1354:
1350:
1344:
1341:
1339:
1336:
1334:
1331:
1330:
1328:
1324:
1318:
1315:
1313:
1310:
1308:
1307:Marcus theory
1305:
1303:
1300:
1298:
1295:
1293:
1290:
1289:
1287:
1284:
1280:
1274:
1271:
1269:
1266:
1264:
1261:
1259:
1258:Isomerization
1256:
1254:
1251:
1250:
1248:
1244:
1238:
1235:
1233:
1232:Cycloaddition
1230:
1228:
1225:
1218:
1215:
1208:
1205:
1204:
1202:
1200:
1196:
1190:
1183:
1180:
1177:
1175:
1172:
1169:
1166:
1165:
1163:
1161:
1157:
1146:
1143:
1142:
1140:
1138:
1134:
1123:
1120:
1113:
1110:
1103:
1100:
1093:
1090:
1083:
1080:
1079:
1077:
1075:
1071:
1067:
1059:
1054:
1052:
1047:
1045:
1040:
1039:
1036:
1029:
1024:
1020:
1017:
1012:
1008:
1007:
995:
991:
987:
983:
979:
975:
971:
967:
959:
951:
947:
943:
939:
935:
931:
924:
916:
912:
908:
906:9780470257623
902:
898:
891:
883:
879:
875:
869:
865:
858:
850:
846:
842:
838:
834:
831:
830:
822:
814:
812:0-07-242458-3
808:
804:
797:
787:
779:
775:
771:
767:
763:
759:
758:
750:
743:
739:
735:
733:9780471854722
729:
725:
724:
719:
713:
705:
701:
697:
693:
692:
684:
680:
671:
668:
667:
661:
659:
649:
645:
643:
642:α-abstraction
639:
638:α-elimination
635:
627:
619:
615:
607:
603:
595:
584:
580:
576:
572:
567:
561:
551:
540:
527:
522:
515:
509:
497:
493:
489:
486:
482:
479:
476:
473:
470:
469:
468:
466:
458:
450:
445:
441:
437:
433:
432:reaction rate
420:
417:
416:
415:
412:
402:
399:
398:
397:
394:
392:
383:
377:
373:
372:
368:
364:
360:
359:
354:
347:
343:
340:of a certain
339:
335:
332:
328:
325:
317:
314:
311:
308:. Therefore,
307:
303:
302:reaction rate
299:
296:
292:
287:
286:deprotonation
284:
282:intermediate.
281:
277:
274:
273:
271:
267:
266:
265:
263:
253:
251:
247:
243:
239:
235:
231:
222:
215:
207:
204:
200:
196:
193:
189:
185:
184:hybridization
181:
178:
174:
171:
167:
166:synperiplanar
163:
159:
155:
152:) need to be
151:
147:
144:
140:
139:reaction rate
136:
133:
130:
126:
125:
124:
121:
119:
118:
112:
108:
104:
94:
92:
84:
81:
77:
73:
69:
62:
61:leaving group
58:
54:
50:
47:in which two
46:
43:is a type of
42:
34:
33:sulfuric acid
30:
26:
21:
3744:Ene reaction
3104:Autoxidation
2965:Degradation
2856:Azo coupling
2766:
2633:Ugi reaction
2233:Ene reaction
2033:Alkynylation
1884:Polyfluorene
1879:Polar effect
1744:Electrophile
1659:Bredt's rule
1629:Baird's rule
1599:Alpha effect
1540:
1379:Molecularity
1159:
1030:at Wikiquote
969:
965:
958:
933:
929:
923:
896:
890:
863:
857:
832:
827:
821:
802:
796:
786:
761:
755:
749:
722:
718:March, Jerry
712:
695:
689:
683:
655:
646:
641:
637:
611:
601:
568:
559:
552:
541:
525:
523:
516:
501:
429:
413:
406:
395:
390:
388:
366:
362:
329:A secondary
269:
261:
259:
256:E1 mechanism
229:
227:
191:
187:
143:second order
122:
114:
110:
106:
102:
100:
97:E2 mechanism
56:
52:
49:substituents
40:
38:
25:cyclohexanol
2243:Ethenolysis
1889:Ring strain
1859:Nucleophile
1684:Clar's rule
1624:Aromaticity
1338:Cage effect
1273:RRKM theory
1189:elimination
618:isocyanides
492:nucleophile
481:temperature
324:1 reactions
280:carbocation
57:E1 reaction
53:E2 reaction
29:cyclohexene
4806:Categories
4527:Ozonolysis
4054:Annulation
3404:Ozonolysis
1523:Topics in
873:1891389319
764:(4): 552.
676:References
539:1 and E1.
276:Ionization
214:2 reaction
4041:reactions
3556:reactions
3051:reactions
2967:reactions
2849:reactions
1991:reactions
1389:Catalysis
1285:reactions
986:1523-7060
950:0002-7863
915:268790870
742:642506595
338:pyrolysis
246:isobutene
91:mechanism
72:pyrolysis
1934:Vinylogy
1604:Annulene
1551:Reagents
994:21366262
882:55600610
849:16417360
720:(1985),
664:See also
575:chlorate
436:halogens
391:scheme 2
295:tertiary
230:scheme 1
170:eclipsed
76:xanthate
35:and heat
1594:A value
766:Bibcode
652:History
485:entropy
444:bromide
346:menthol
242:ethanol
150:halogen
117:Pi bond
80:acetate
1064:Basic
992:
984:
948:
913:
903:
880:
870:
847:
809:
740:
730:
698:: 33.
628:, :CCl
440:iodide
83:esters
1292:Redox
1128:Acyl)
510:(an S
236:with
31:with
1181:(E2)
1170:(E1)
990:PMID
982:ISSN
946:ISSN
911:OCLC
901:ISBN
878:OCLC
868:ISBN
845:PMID
807:ISBN
738:OCLC
728:ISBN
640:and
560:tert
442:and
430:The
407:If S
300:The
177:base
160:has
137:The
115:C=C
109:and
78:and
1151:Ar)
1108:Ar)
974:doi
938:doi
934:103
837:doi
833:128
774:doi
700:doi
616:or
344:of
240:in
190:to
141:is
120:).
74:of
39:An
27:to
4808::
1219:(A
1209:(A
1147:(S
1124:(S
1118:i)
1114:(S
1104:(S
1098:2)
1094:(S
1088:1)
1084:(S
988:.
980:.
970:13
968:.
944:.
932:.
909:.
876:.
843:.
772:.
762:85
760:.
736:,
694:.
529:aH
438:,
272:.
252:.
192:sp
188:sp
93:.
67:CB
65:E1
1516:e
1509:t
1502:v
1223:)
1221:N
1213:)
1211:E
1187:i
1185:E
1149:E
1126:N
1116:N
1106:N
1096:N
1086:N
1057:e
1050:t
1043:v
996:.
976::
952:.
940::
917:.
884:.
851:.
839::
815:.
780:.
776::
768::
706:.
702::
696:5
630:2
622:3
591:N
587:N
564:N
555:N
548:N
544:N
537:N
533:N
526:K
519:N
512:N
504:N
487:)
465:1
463:N
461:S
457:2
455:N
453:S
409:N
367:B
363:A
348::
322:N
320:S
212:N
210:S
194:.
131:.
89:i
87:E
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