293:) will form. The E1cB mechanism is just one of three types of elimination reaction. The other two elimination reactions are E1 and E2 reactions. Although the mechanisms are similar, they vary in the timing of the deprotonation of the α-carbon and the loss of the leaving group. E1 stands for unimolecular elimination, and E2 stands for bimolecular elimination. In an E1 mechanism, the molecule contains a good leaving group that departs before deprotonation of the α-carbon. This results in the formation of a carbocation intermediate. The carbocation is then deprotonated resulting in the formation of a new pi bond. The molecule involved must also have a very good leaving group such as bromine or chlorine, and it should have a relatively less acidic α-carbon.
122:
481:
297:
109:
particularly acidic and a strong base is absent. Thus, in the E1 mechanism, the leaving group leaves first to generate a carbocation. Due to the presence of an empty p orbital after departure of the leaving group, the hydrogen on the neighboring carbon becomes much more acidic, allowing it to then be removed by the weak base in the second step. In an E2 reaction, the presence of a strong base and a good leaving group allows proton abstraction by the base and the departure of the leaving group to occur simultaneously, leading to a concerted
945:
259:
917:
696:
20:
108:
E1cB should be thought of as being on one end of a continuous spectrum, which includes the E1 mechanism at the opposite end and the E2 mechanism in the middle. The E1 mechanism usually has the opposite characteristics: the leaving group is a good one (like -OTs or -Br), while the hydrogen is not
933:
In this report, a photochemically induced decarboxylation reaction generates a carbanion intermediate, which subsequently eliminates the leaving group. The reaction is unique from other forms of E1cB since it does not require a base to generate the carbanion. The carbanion formation step is
873:
and E2 mechanisms. C can also be used to probe the nature of the transition state structure. The use of C can be used to study the formation of the carbanion as well as study its lifetime which can not only show that the reaction is a two-step E1cB mechanism (as opposed to the concerted E2
824:
type mechanism. Recall, in this mechanism protonation of the carbanion (either by the conjugate acid or by solvent) is faster than loss of the leaving group. This means after the carbanion is formed, it will quickly remove a proton from the solvent to form the starting
168:. In general it can be claimed that an electron withdrawing group on the substrate, a strong base, a poor leaving group and a polar solvent triggers the E1cB mechanism. An example of an E1cB mechanism that has a stable transition state can be seen in the degradation of
908:
of the starting material, and is one of the intermediates in the reaction. This enolate then acts as a nucleophile and can attack an electrophilic aldehyde. The Aldol product is then deprotonated forming another enolate followed by the elimination of water in an E1cB
1145:
Baciocchi, Enrico; Ruzziconi, Renzo; Sebastiani, Giovanni
Vittorio (1 August 1982). "Concerted and stepwise mechanisms in the eliminations from 1,2-dihaloacenaphthenes promoted by potassium tert-butoxide and potassium ethoxide in the corresponding alcohols".
308:
step. Molecules that undergo E2-elimination mechanisms have more acidic α-carbons than those that undergo E1 mechanisms, but their α-carbons are not as acidic as those of molecules that undergo E1cB mechanisms. The key difference between the
494:
355:
mechanism. The following table summarizes the key differences between the three elimination reactions; however, the best way to identify which mechanism is playing a key role in a particular reaction involves the application of
865:
and other compounds in medical research. This experiment is very useful in determining whether or not the loss of the leaving group is the rate-determining step in the mechanism and can help distinguish between
827:
If the reactant contains deuterium at the ÎČ position, a primary kinetic isotope effect indicates that deprotonation is rate determining. Of the three E1cB mechanisms, this result is only consistent with the
499:
4958:
149:
transition state, such as a carbanion. The greater the stability of this transition state, the more the mechanism will favor an E1cB mechanism. This transition state can be stabilized through
43:(such as -OH or -OR) is a relatively poor one. Usually a moderate to strong base is present. E1cB is a two-step process, the first step of which may or may not be reversible. First, a
874:
mechanism), but it can also address the lifetime and stability of the transition state structure which can further distinguish between the three different types of E1cB mechanisms.
817:
OD), then the exchange of protons into the starting material can be monitored. If the recovered starting material contains deuterium, then the reaction is most likely undergoing an
715:
is when the carbanion is stable and/or a strong base is used in excess of the substrate, making deprotonation irreversible, followed by rate-determining loss of the leaving group (k
351:
even though chlorine is a much better leaving group. This provides evidence that the carbanion is formed because the products are not possible through the most stable concerted
913:. Aldol reactions are a key reaction in organic chemistry because they provide a means of forming carbon-carbon bonds, allowing for the synthesis of more complex molecules.
4074:
4019:
4787:
705:
will be exhibited. E1cB mechanisms kinetics can vary slightly based on the rate of each step. As a result, the E1cB mechanism can be broken down into three categories:
4129:
691:{\displaystyle {\begin{aligned}{\frac {\ce {d}}{{\ce {d}}t}}&={\frac {k_{1}k_{2}{\ce {}}}{k_{-1}+k_{2}}}\\{\ce {rate}}&=k_{\ce {obs}}{\ce {}}\end{aligned}}}
4279:
2913:
5008:
1346:
4782:
732:
is when the first step is reversible but the formation of product is slower than reforming the starting material, this again results from a slow second step (k
3884:
2608:
3654:
1805:
4454:
2398:
4549:
2653:
4529:
4024:
3191:
3072:
2628:
1075:
Ouertani, Randa; El
Atrache, Latifa Latrous; Hamida, Nejib Ben (2013). "Alkaline hydrolysis of ethiofencarb: Kinetic study and mechanism degradation".
4619:
861:
is a relatively poor leaving group, and it is often employed in E1cB mechanisms. Fluorine kinetic isotope effects are also applied in the labeling of
4374:
1841:
3206:
4852:
4309:
4802:
4414:
4394:
4354:
3161:
4948:
4873:
4757:
3369:
2773:
2104:
1217:
1059:
1034:
4943:
4772:
4429:
4284:
3914:
3759:
2996:
4119:
3609:
3284:
1558:
5023:
4807:
3829:
1285:
Lukeman, Matthew; Scaiano, Juan C. (2005). "Carbanion-Mediated
Photocages: Rapid and Efficient Photorelease with Aqueous Compatibility".
1233:
Matsson, Olle; MacMillar, Susanna (September 2007). "Isotope effects for fluorine-18 and carbon-11 in the study of reaction mechanisms".
1435:
1110:
Hine, Jack; Burske, Norbert W.; Hine, Mildred; Langford, Paul B. (1957). "The
Relative Rates of Formation of Carbanions by Haloforms1".
4384:
5018:
4732:
4594:
4349:
1392:
4908:
4379:
4294:
4264:
4244:
4109:
4104:
3479:
3404:
3047:
3001:
2868:
2129:
1699:
4847:
1339:
1269:
304:
In an E2-elimination reaction, both the deprotonation of the α-carbon and the loss of the leaving group occur simultaneously in one
5013:
4973:
4923:
4399:
4149:
4079:
2568:
4609:
4214:
3107:
2828:
4599:
2139:
4767:
4524:
4474:
3264:
3196:
3087:
2663:
2418:
2343:
2124:
4479:
4289:
3764:
3674:
1798:
5053:
4837:
4777:
4179:
4154:
4064:
3644:
3524:
2558:
2054:
5102:
4938:
4424:
4219:
2488:
1607:
1602:
1412:
51:. The lone pair of electrons on the anion then moves to the neighboring atom, thus expelling the leaving group and forming a
5043:
4629:
4139:
3649:
3594:
3439:
3399:
3231:
2986:
2703:
2553:
1767:
121:
5003:
4564:
4519:
4009:
3864:
1772:
474:
are essential. The best ways to identify the E1cB mechanism involves the use of rate laws and the kinetic isotope effect.
199:. In addition to containing an acidic hydrogen on the ÎČ-carbon, a relatively poor leaving group is also necessary. A bad
5038:
4953:
4812:
4727:
4624:
3699:
3354:
3022:
2433:
1994:
5107:
4928:
4903:
4888:
4584:
4449:
4404:
4169:
3714:
3564:
2778:
2458:
2403:
1332:
4933:
4878:
4409:
3824:
3539:
3534:
3027:
2843:
2833:
2548:
2408:
2358:
2353:
2328:
2234:
266:
illustrating the presence of a stable anion due to resonance between the amide functional group and the carbonyl group.
129:
There are two main requirements to have a reaction proceed down an E1cB mechanistic pathway. The compound must have an
4988:
4589:
4509:
4124:
4089:
3934:
3359:
3319:
3216:
2991:
2743:
2688:
2288:
1999:
1989:
1964:
480:
4963:
4664:
4469:
3904:
3469:
3444:
3384:
2976:
2683:
2333:
477:
The rate law that governs E1cB mechanisms is relatively simple to determine. Consider the following reaction scheme.
2518:
488:
Assuming that there is a steady-state carbanion concentration in the mechanism, the rate law for an E1cB mechanism.
4254:
3789:
3241:
2463:
2428:
2024:
1959:
1791:
1737:
1427:
4822:
4444:
3504:
3429:
2953:
2788:
2473:
2249:
2209:
1954:
5063:
4968:
4702:
4674:
4644:
4559:
4489:
4419:
4339:
4239:
4199:
3894:
3514:
2813:
2808:
2270:
2134:
1364:
5028:
4898:
4762:
4604:
4464:
3984:
2958:
2508:
2468:
2219:
296:
4918:
4514:
4484:
4359:
4314:
4144:
4054:
3869:
3859:
3689:
3246:
3186:
3151:
2938:
2898:
2673:
2543:
2059:
2049:
1979:
1694:
216:
4494:
3474:
2498:
2044:
1924:
145:. The first step of an E1cB mechanism is the deprotonation of the ÎČ-carbon, resulting in the formation of an
4707:
4998:
4857:
4649:
4574:
4554:
4274:
4224:
4084:
4049:
3989:
3919:
3221:
3201:
2933:
2853:
2748:
2708:
2678:
2613:
2483:
2393:
2383:
2259:
1969:
1742:
1543:
211:
pathway. Some examples of compounds that contain poor leaving groups and can undergo the E1cB mechanism are
944:
320:
as opposed to one concerted mechanism. Studies have been shown that the pathways differ by using different
4737:
4459:
4209:
4189:
4164:
4114:
4029:
4004:
3959:
3929:
3909:
3879:
3844:
3799:
3774:
3749:
3634:
3559:
3339:
3032:
2968:
2768:
2493:
2413:
2099:
2074:
1851:
1846:
1497:
785:
774:
453:
5073:
3819:
2443:
4659:
4614:
4329:
4299:
4269:
4204:
4184:
4099:
4094:
4059:
4014:
3999:
3994:
3974:
3964:
3899:
3889:
3769:
3289:
3092:
2668:
2623:
2453:
2189:
1909:
1871:
1727:
1659:
1517:
1507:
957:
The E1cB-elimination reaction is an important reaction in biology. For example, the penultimate step of
857:
Another way that the kinetic isotope effect can help distinguish E1cB mechanisms involves the use of F.
484:
An example of an E1cB-elimination mechanism with a generic leaving group (LG), and ethoxide as the base.
317:
232:
165:
142:
134:
102:
2119:
2114:
456:. These techniques can also help further differentiate between E1cB, E1, and E2-elimination reactions.
4712:
39:
which occurs under basic conditions, where the hydrogen to be removed is relatively acidic, while the
4842:
4792:
4742:
4722:
4569:
4544:
4259:
4249:
4134:
3949:
3944:
3874:
3659:
3459:
3419:
3349:
3314:
3269:
3236:
3102:
3077:
3057:
2878:
2838:
2798:
2763:
2693:
2448:
2318:
2293:
1831:
1722:
1450:
982:
910:
352:
310:
276:
208:
154:
84:
36:
5058:
5048:
5033:
4679:
4654:
4639:
4634:
4364:
4319:
4304:
4194:
4174:
4069:
3954:
3939:
3784:
3729:
3719:
3709:
3684:
3449:
3324:
3299:
3211:
3067:
3052:
3037:
2893:
2858:
2803:
2573:
2423:
2368:
2239:
2154:
2014:
1939:
1732:
1664:
1649:
1592:
966:
212:
2084:
4797:
4747:
4717:
4579:
4369:
4159:
4044:
3979:
3969:
3734:
3664:
3629:
3624:
3604:
3599:
3544:
3454:
3304:
3166:
3156:
3062:
2848:
2793:
2723:
2643:
2538:
2438:
2373:
2298:
2144:
2009:
1944:
1757:
1527:
1356:
987:
962:
889:
305:
1929:
285:
from a pair of atoms in a compound. Alkene, alkynes, or similar heteroatom variations (such as
258:
4534:
3854:
3739:
3704:
3669:
3614:
3569:
3529:
3484:
3464:
3414:
3409:
3379:
3364:
3274:
3181:
3117:
3082:
2908:
2783:
2658:
2583:
2563:
2478:
2313:
2308:
2254:
2164:
2069:
2029:
1984:
1866:
1861:
1826:
1752:
1747:
1709:
1654:
1573:
1553:
1489:
1310:
1302:
1265:
1213:
1190:
1127:
1092:
1055:
1030:
862:
702:
471:
470:
When trying to experimentally determine whether or not a reaction follows the E1cB mechanism,
445:
439:
357:
235:
hybridization creates slightly more acidic protons. Although this mechanism is not limited to
192:
1026:
1019:
5068:
4913:
4883:
4827:
4752:
4684:
4439:
4389:
4234:
4039:
3814:
3809:
3754:
3744:
3519:
3329:
3309:
3279:
3176:
3112:
3097:
2928:
2883:
2873:
2863:
2758:
2738:
2733:
2718:
2713:
2593:
2588:
2528:
2513:
2503:
2348:
2338:
2204:
2194:
2184:
2094:
2089:
2064:
2004:
1856:
1815:
1684:
1633:
1587:
1294:
1242:
1182:
1155:
1119:
1084:
150:
110:
44:
749:
is when the first step is slow, but once the anion is formed the product quickly follows (k
4978:
4669:
4504:
4499:
3794:
3779:
3724:
3679:
3639:
3589:
3554:
3549:
3494:
3489:
3424:
3374:
3294:
3122:
3006:
2981:
2943:
2918:
2903:
2888:
2823:
2698:
2648:
2638:
2618:
2578:
2388:
2378:
2363:
2159:
2079:
1904:
1899:
1762:
1674:
1623:
1949:
1919:
916:
4983:
4893:
4832:
3924:
3834:
3804:
3579:
3434:
3171:
2948:
2818:
2633:
2603:
2303:
2199:
1974:
1836:
1469:
1458:
920:
An aldol condensation reaction is one of the most common examples of an E1cB mechanism.
905:
883:
97:
5096:
4993:
4694:
4539:
4434:
4229:
3619:
3584:
3574:
3509:
3499:
3389:
3226:
3042:
2753:
2728:
2598:
2244:
2229:
2214:
2109:
2039:
2019:
1934:
1717:
1689:
1597:
1548:
1522:
893:
465:
449:
348:
324:
200:
138:
91:
refers to the fact that the rate-determining step of this reaction only involves one
40:
300:
Example of the preferential elimination of fluorine in an E1cB-elimination reaction.
4034:
3394:
3146:
2923:
2523:
2323:
2174:
2169:
2034:
1889:
1669:
1475:
1382:
1372:
391:
Simultaneous removal of proton, formation of double bond, and loss of leaving group
263:
252:
169:
92:
1173:
McLennan, D. J. (1967). "The carbanion mechanism of olefin-forming elimination".
2533:
2179:
2149:
1914:
1628:
1563:
992:
282:
176:
56:
52:
448:
are essential. The best way to identify the E1cB mechanism involves the use of
444:
When trying to determine whether or not a reaction follows the E1cB mechanism,
271:
Distinguishing E1cB-elimination reactions from E1- and E2-elimination reactions
4817:
4344:
3694:
1783:
958:
240:
204:
19:
1306:
1194:
1131:
1096:
1679:
1324:
997:
810:
314:
180:
173:
161:
24:
1314:
219:. It has also been suggested that the E1cB mechanism is more common among
207:
of the molecule. As a result, the compound will likely proceed through an
2224:
1894:
1186:
897:
858:
344:
340:
328:
286:
244:
196:
158:
1159:
1123:
1884:
1212:(6th ed.). Hoboken, N.J.: Wiley-Interscience. pp. 1488â1493.
1210:
March's advanced organic chemistry reactions, mechanisms, and structure
1054:(6th ed.). Hoboken, N.J.: Wiley-Interscience. pp. 1488â1493.
1052:
March's advanced organic chemistry reactions, mechanisms, and structure
970:
901:
332:
321:
1298:
1246:
1088:
248:
236:
228:
224:
220:
888:
The most well known reaction that undergoes E1cB elimination is the
1582:
943:
915:
479:
336:
295:
290:
257:
188:
184:
146:
120:
48:
23:
An example of the E1cB reaction mechanism in the degradation of a
18:
961:
involves an E1cB mechanism. This step involves the conversion of
203:
is necessary because a good leaving group will leave before the
130:
47:
abstracts the relatively acidic proton to generate a stabilized
2268:
1787:
1328:
1402:
948:
E1cB reaction mechanism through photo-induced decarboxylation.
929:
A photochemical version of E1cB has been reported by
Lukeman
231:
to alkene. One possible explanation for this is that the
125:α and ÎČ assignments in a molecule with leaving group, LG
105:, which is the conjugate base of the starting material.
757:). This leads to an irreversible first step but unlike
1235:
Journal of
Labelled Compounds and Radiopharmaceuticals
497:
281:
All elimination reactions involve the removal of two
4959:
ErlenmeyerâPlöchl azlactone and amino-acid synthesis
4866:
4693:
4328:
3843:
3338:
3255:
3135:
3015:
2967:
2277:
1708:
1642:
1616:
1572:
1536:
1488:
1449:
1426:
1363:
892:reaction under basic conditions. This involves the
842:and leaving group departure is rate determining in
835:mechanism, since the isotope is already removed in
1018:
690:
4020:Divinylcyclopropane-cycloheptadiene rearrangement
1264:. New Jersey: Prentice Hall. pp. 1056â1066.
183:in Earth's atmosphere. Upon deprotonation of the
1021:The Art of Writing Reasonable Organic Mechanisms
434:Chemical kinetics of E1cB-elimination mechanisms
934:irreversible, and should thus be classified as
4280:Thermal rearrangement of aromatic hydrocarbons
2914:Thermal rearrangement of aromatic hydrocarbons
239:eliminations. It has been observed with other
5009:Lectka enantioselective beta-lactam synthesis
1799:
1340:
8:
4788:Inverse electron-demand DielsâAlder reaction
2609:Heterogeneous metal catalyzed cross-coupling
83:refers to the fact that the mechanism is an
4130:Lobry de BruynâVan Ekenstein transformation
701:From this equation, it is clear the second
4690:
2964:
2265:
1806:
1792:
1784:
1347:
1333:
1325:
1077:International Journal of Chemical Kinetics
900:group that results in the formation of an
4620:Petrenko-Kritschenko piperidone synthesis
4075:FritschâButtenbergâWiechell rearrangement
672:
661:
660:
654:
638:
625:
604:
592:
574:
563:
562:
556:
546:
539:
521:
508:
502:
498:
496:
101:refers to the formation of the carbanion
4783:Intramolecular DielsâAlder cycloaddition
1287:Journal of the American Chemical Society
1112:Journal of the American Chemical Society
809:. If the solvent is protic and contains
362:
1009:
4803:Metal-centered cycloaddition reactions
4455:DebusâRadziszewski imidazole synthesis
2399:BodrouxâChichibabin aldehyde synthesis
1373:Unimolecular nucleophilic substitution
4949:Diazoalkane 1,3-dipolar cycloaddition
4853:Vinylcyclopropane (5+2) cycloaddition
4758:Diazoalkane 1,3-dipolar cycloaddition
4530:HurdâMori 1,2,3-thiadiazole synthesis
4025:DowdâBeckwith ring-expansion reaction
3192:HurdâMori 1,2,3-thiadiazole synthesis
2105:LFER solvent coefficients (data page)
1383:Bimolecular nucleophilic substitution
7:
3760:Sharpless asymmetric dihydroxylation
2997:Methoxymethylenetriphenylphosphorane
764:, deprotonation is rate determining.
3885:AllenâMillarâTrippett rearrangement
1436:Electrophilic aromatic substitution
1175:Quarterly Reviews, Chemical Society
784:Deuterium exchange and a deuterium
191:is relatively stable because it is
5024:Nitrone-olefin (3+2) cycloaddition
5019:Niementowski quinazoline synthesis
4808:Nitrone-olefin (3+2) cycloaddition
4733:Azide-alkyne Huisgen cycloaddition
4595:Niementowski quinazoline synthesis
4350:Azide-alkyne Huisgen cycloaddition
3655:MeerweinâPonndorfâVerley reduction
3207:LeimgruberâBatcho indole synthesis
1403:Nucleophilic internal substitution
1393:Nucleophilic aromatic substitution
14:
4848:Trimethylenemethane cycloaddition
4550:JohnsonâCoreyâChaykovsky reaction
4415:CadoganâSundberg indole synthesis
4395:BohlmannâRahtz pyridine synthesis
4355:BaeyerâEmmerling indole synthesis
3162:CadoganâSundberg indole synthesis
2654:JohnsonâCoreyâChaykovsky reaction
904:. The enolate is the very stable
4944:CookâHeilbron thiazole synthesis
4773:Hexadehydro DielsâAlder reaction
4600:Niementowski quinoline synthesis
4430:CookâHeilbron thiazole synthesis
4375:BischlerâMöhlau indole synthesis
4285:TiffeneauâDemjanov rearrangement
3915:BakerâVenkataraman rearrangement
3073:HornerâWadsworthâEmmons reaction
2744:Mizoroki-Heck vs. Reductive Heck
2629:HornerâWadsworthâEmmons reaction
2140:Neighbouring group participation
1148:The Journal of Organic Chemistry
87:and will lose two substituents.
4480:Fiesselmann thiophene synthesis
4310:WestphalenâLettrĂ© rearrangement
4290:Vinylcyclopropane rearrangement
4120:KornblumâDeLaMare rearrangement
3765:Epoxidation of allylic alcohols
3675:Noyori asymmetric hydrogenation
3610:KornblumâDeLaMare rearrangement
3285:GallagherâHollander degradation
1559:LindemannâHinshelwood mechanism
1025:. New York: Springer. pp.
313:vs E1cb pathways is a distinct
4939:Chichibabin pyridine synthesis
4425:Chichibabin pyridine synthesis
4385:BlumâIttah aziridine synthesis
4220:Ring expansion and contraction
2489:Cross dehydrogenative coupling
1608:Outer sphere electron transfer
1603:Inner sphere electron transfer
1413:Nucleophilic acyl substitution
813:in place of hydrogen (e.g., CH
679:
673:
668:
662:
615:
601:
581:
575:
570:
564:
515:
509:
59:. The name of the mechanism -
1:
4909:BischlerâNapieralski reaction
4867:Heterocycle forming reactions
4520:Hemetsberger indole synthesis
4380:BischlerâNapieralski reaction
4295:WagnerâMeerwein rearrangement
4265:SommeletâHauser rearrangement
4245:SeyferthâGilbert homologation
4110:IrelandâClaisen rearrangement
4105:HofmannâMartius rearrangement
3865:2,3-sigmatropic rearrangement
3480:CoreyâWinter olefin synthesis
3405:BartonâMcCombie deoxygenation
3048:CoreyâWinter olefin synthesis
3002:SeyferthâGilbert homologation
2869:SeyferthâGilbert homologation
1773:Diffusion-controlled reaction
5014:LehmstedtâTanasescu reaction
4974:GabrielâColman rearrangement
4929:Bucherer carbazole synthesis
4924:BorscheâDrechsel cyclization
4904:Bernthsen acridine synthesis
4889:Bamberger triazine synthesis
4874:AlgarâFlynnâOyamada reaction
4585:Nazarov cyclization reaction
4450:De Kimpe aziridine synthesis
4405:Bucherer carbazole synthesis
4400:BorscheâDrechsel cyclization
4170:Nazarov cyclization reaction
4150:MeyerâSchuster rearrangement
4080:GabrielâColman rearrangement
3830:WolffensteinâBöters reaction
3715:Reduction of nitro compounds
3565:Grundmann aldehyde synthesis
3370:AlgarâFlynnâOyamada reaction
2779:Olefin conversion technology
2774:NozakiâHiyamaâKishi reaction
2569:GabrielâColman rearrangement
2459:Claisen-Schmidt condensation
2404:Bouveault aldehyde synthesis
969:, facilitated by the enzyme
179:that has a relatively short
4989:Hantzsch pyridine synthesis
4768:Enoneâalkene cycloadditions
4590:Nenitzescu indole synthesis
4510:Hantzsch pyridine synthesis
4475:FerrarioâAckermann reaction
4125:Kowalski ester homologation
4090:Halogen dance rearrangement
3935:Benzilic acid rearrangement
3360:Akabori amino-acid reaction
3320:Von Braun amide degradation
3265:BarbierâWieland degradation
3217:Nenitzescu indole synthesis
3197:KharaschâSosnovsky reaction
3088:JuliaâKocienski olefination
2992:Kowalski ester homologation
2689:Kowalski ester homologation
2664:JuliaâKocienski olefination
2419:CadiotâChodkiewicz coupling
2344:Aza-BaylisâHillman reaction
2289:Acetoacetic ester synthesis
2000:Dynamic binding (chemistry)
1990:Conrotatory and disrotatory
1965:Charge remote fragmentation
1428:Electrophilic substitutions
896:of a compound containing a
788:can help distinguish among
5124:
5054:RobinsonâGabriel synthesis
5004:Kröhnke pyridine synthesis
4838:Retro-DielsâAlder reaction
4778:Imine DielsâAlder reaction
4565:Kröhnke pyridine synthesis
4180:NewmanâKwart rearrangement
4155:MislowâEvans rearrangement
4065:FischerâHepp rearrangement
4010:Di-Ï-methane rearrangement
3790:Stephen aldehyde synthesis
3525:EschweilerâClarke reaction
3242:Williamson ether synthesis
2559:FujiwaraâMoritani reaction
2464:Combes quinoline synthesis
2429:Carbonyl olefin metathesis
2130:More O'FerrallâJencks plot
2055:GrunwaldâWinstein equation
2025:Electron-withdrawing group
1960:Catalytic resonance theory
1738:Energy profile (chemistry)
1700:More O'FerrallâJencks plot
1365:Nucleophilic substitutions
881:
772:
463:
437:
274:
5064:Urech hydantoin synthesis
5044:PomeranzâFritsch reaction
4969:Fischer oxazole synthesis
4703:1,3-Dipolar cycloaddition
4675:Urech hydantoin synthesis
4645:Reissert indole synthesis
4630:PomeranzâFritsch reaction
4560:Knorr quinoline synthesis
4490:Fischer oxazole synthesis
4420:Camps quinoline synthesis
4340:1,3-Dipolar cycloaddition
4240:Semipinacol rearrangement
4215:RambergâBĂ€cklund reaction
4200:Piancatelli rearrangement
4140:McFadyenâStevens reaction
3895:Alpha-ketol rearrangement
3650:McFadyenâStevens reaction
3595:KilianiâFischer synthesis
3515:Elbs persulfate oxidation
3440:BouveaultâBlanc reduction
3400:BaeyerâVilliger oxidation
3232:SchottenâBaumann reaction
3108:RambergâBĂ€cklund reaction
2987:KilianiâFischer synthesis
2829:RambergâBĂ€cklund reaction
2814:Pinacol coupling reaction
2809:Piancatelli rearrangement
2704:LiebeskindâSrogl coupling
2554:FujimotoâBelleau reaction
2271:List of organic reactions
2135:Negative hyperconjugation
1880:
1822:
1768:MichaelisâMenten kinetics
853:Fluorine-19 and carbon-11
33:E1cB elimination reaction
5039:PictetâSpengler reaction
4954:EinhornâBrunner reaction
4919:Boger pyridine synthesis
4813:Oxo-DielsâAlder reaction
4728:Aza-DielsâAlder reaction
4625:PictetâSpengler reaction
4525:HofmannâLöffler reaction
4515:Hegedus indole synthesis
4485:Fischer indole synthesis
4360:Bartoli indole synthesis
4315:Willgerodt rearrangement
4145:McLafferty rearrangement
4055:Ferrier carbocyclization
3870:2,3-Wittig rearrangement
3860:1,2-Wittig rearrangement
3700:ParikhâDoering oxidation
3690:Oxygen rebound mechanism
3355:AdkinsâPeterson reaction
3247:Yamaguchi esterification
3187:Hegedus indole synthesis
3152:Bartoli indole synthesis
3023:BamfordâStevens reaction
2939:Weinreb ketone synthesis
2899:Stork enamine alkylation
2674:Knoevenagel condensation
2544:Ferrier carbocyclization
2434:CastroâStephens coupling
2060:Hammett acidity function
2050:Free-energy relationship
1995:CurtinâHammett principle
1980:Conformational isomerism
1695:Potential energy surface
1574:Electron/Proton transfer
1459:Unimolecular elimination
388:Carbocation intermediate
331:as a better stabilizing
247:in the elimination of a
4999:Knorr pyrrole synthesis
4934:BuchererâBergs reaction
4879:AllanâRobinson reaction
4858:Wagner-Jauregg reaction
4650:Ring-closing metathesis
4575:Larock indole synthesis
4555:Knorr pyrrole synthesis
4410:BuchererâBergs reaction
4275:Stieglitz rearrangement
4255:SkattebĂžl rearrangement
4225:Ring-closing metathesis
4085:Group transfer reaction
4050:Favorskii rearrangement
3990:Cornforth rearrangement
3920:Bamberger rearrangement
3825:WolffâKishner reduction
3645:MarkĂłâLam deoxygenation
3540:FlemingâTamao oxidation
3535:FischerâTropsch process
3222:Oxymercuration reaction
3202:Knorr pyrrole synthesis
3028:BartonâKellogg reaction
2934:Wagner-Jauregg reaction
2854:Ring-closing metathesis
2844:ReimerâTiemann reaction
2834:RauhutâCurrier reaction
2749:Nef isocyanide reaction
2709:Malonic ester synthesis
2679:Knorr pyrrole synthesis
2614:High dilution principle
2549:FriedelâCrafts reaction
2484:Cross-coupling reaction
2409:BuchererâBergs reaction
2394:Blanc chloromethylation
2384:Blaise ketone synthesis
2359:BaylisâHillman reaction
2354:BartonâKellogg reaction
2329:AllanâRobinson reaction
2235:WoodwardâHoffmann rules
1970:Charge-transfer complex
1743:Transition state theory
1544:Intramolecular reaction
1470:Bimolecular elimination
1208:Smith, Michael (2007).
1050:Smith, Michael (2007).
1017:Grossman, R.B. (2008).
394:Carbanion intermediate
113:in a one-step process.
4964:FeistâBenary synthesis
4738:Bradsher cycloaddition
4708:4+4 Photocycloaddition
4665:SimmonsâSmith reaction
4610:PaternĂČâBĂŒchi reaction
4470:FeistâBenary synthesis
4460:Dieckmann condensation
4210:Pummerer rearrangement
4190:Oxy-Cope rearrangement
4165:Myers allene synthesis
4115:Jacobsen rearrangement
4030:Electrocyclic reaction
4005:Demjanov rearrangement
3960:Buchner ring expansion
3930:Beckmann rearrangement
3910:Aza-Cope rearrangement
3905:ArndtâEistert reaction
3880:Alkyne zipper reaction
3800:Transfer hydrogenation
3775:Sharpless oxyamination
3750:Selenoxide elimination
3635:Lombardo methylenation
3560:Griesbaum coozonolysis
3470:CoreyâItsuno reduction
3445:BoylandâSims oxidation
3385:AngeliâRimini reaction
3033:Boord olefin synthesis
2977:ArndtâEistert reaction
2969:Homologation reactions
2769:Nitro-Mannich reaction
2684:KolbeâSchmitt reaction
2494:Cross-coupling partner
2414:Buchner ring expansion
2334:ArndtâEistert reaction
2100:Kinetic isotope effect
1847:Rearrangement reaction
1537:Unimolecular reactions
1498:Electrophilic addition
949:
921:
786:kinetic isotope effect
775:Kinetic isotope effect
769:Kinetic isotope effect
692:
485:
454:kinetic isotope effect
301:
267:
137:and a relatively poor
126:
28:
27:under basic conditions
5103:Elimination reactions
4823:PausonâKhand reaction
4660:Sharpless epoxidation
4615:Pechmann condensation
4495:FriedlÀnder synthesis
4445:DavisâBeirut reaction
4300:Wallach rearrangement
4270:Stevens rearrangement
4205:Pinacol rearrangement
4185:Overman rearrangement
4100:Hofmann rearrangement
4095:Hayashi rearrangement
4060:Ferrier rearrangement
4015:Dimroth rearrangement
4000:Curtius rearrangement
3995:Criegee rearrangement
3975:Claisen rearrangement
3965:Carroll rearrangement
3900:Amadori rearrangement
3890:Allylic rearrangement
3770:Sharpless epoxidation
3505:DessâMartin oxidation
3430:BohnâSchmidt reaction
3290:Hofmann rearrangement
3093:Kauffmann olefination
3016:Olefination reactions
2954:WurtzâFittig reaction
2789:PalladiumâNHC complex
2669:Kauffmann olefination
2624:Homologation reaction
2474:CoreyâHouse synthesis
2454:Claisen rearrangement
2250:YukawaâTsuno equation
2210:SwainâLupton equation
2190:Spherical aromaticity
2125:MöbiusâHĂŒckel concept
1910:Aromatic ring current
1872:Substitution reaction
1728:Rate-determining step
1660:Reactive intermediate
1518:Free-radical addition
1508:Nucleophilic addition
1451:Elimination reactions
947:
919:
693:
483:
405:Strongly basic media
399:Strongly acidic media
299:
261:
195:with the neighboring
124:
22:
5029:PaalâKnorr synthesis
4899:BartonâZard reaction
4843:Staudinger synthesis
4793:Ketene cycloaddition
4763:DielsâAlder reaction
4743:Cheletropic reaction
4723:Alkyne trimerisation
4605:PaalâKnorr synthesis
4570:Kulinkovich reaction
4545:Jacobsen epoxidation
4465:DielsâAlder reaction
4260:Smiles rearrangement
4250:Sigmatropic reaction
4135:Lossen rearrangement
3985:CoreyâFuchs reaction
3950:Boekelheide reaction
3945:Bergmann degradation
3875:Achmatowicz reaction
3660:Methionine sulfoxide
3460:Clemmensen reduction
3420:Bergmann degradation
3350:Acyloin condensation
3315:Strecker degradation
3270:Bergmann degradation
3237:Ullmann condensation
3103:Peterson olefination
3078:Hydrazone iodination
3058:Elimination reaction
2959:ZinckeâSuhl reaction
2879:Sonogashira coupling
2839:Reformatsky reaction
2799:Peterson olefination
2764:Nierenstein reaction
2694:Kulinkovich reaction
2509:DielsâAlder reaction
2469:CoreyâFuchs reaction
2449:Claisen condensation
2319:Alkyne trimerisation
2294:Acyloin condensation
2260:ÎŁ-bishomoaromaticity
2220:ThorpeâIngold effect
1832:Elimination reaction
1723:Equilibrium constant
1187:10.1039/qr9672100490
983:Elimination reaction
911:dehydration reaction
863:Radiopharmaceuticals
495:
416:Poor leaving groups
277:Elimination reaction
85:elimination reaction
37:elimination reaction
5108:Reaction mechanisms
5049:Prilezhaev reaction
5034:Pellizzari reaction
4713:(4+3) cycloaddition
4680:Van Leusen reaction
4655:Robinson annulation
4640:Pschorr cyclization
4635:Prilezhaev reaction
4365:Bergman cyclization
4320:Wolff rearrangement
4305:Weerman degradation
4195:Pericyclic reaction
4175:Neber rearrangement
4070:Fries rearrangement
3955:Brook rearrangement
3940:Bergman cyclization
3785:Staudinger reaction
3730:Rosenmund reduction
3720:Reductive amination
3685:Oppenauer oxidation
3475:CoreyâKim oxidation
3450:Cannizzaro reaction
3325:Weerman degradation
3300:Isosaccharinic acid
3212:Mukaiyama hydration
3068:Hofmann elimination
3053:Dehydrohalogenation
3038:Chugaev elimination
2859:Robinson annulation
2804:Pfitzinger reaction
2574:Gattermann reaction
2519:WulffâDötz reaction
2499:DakinâWest reaction
2424:Carbonyl allylation
2369:Bergman cyclization
2155:Kennedy J. P. Orton
2075:Hammond's postulate
2045:FlippinâLodge angle
2015:Electromeric effect
1940:Beta-silicon effect
1925:BakerâNathan effect
1733:Reaction coordinate
1665:Radical (chemistry)
1650:Elementary reaction
1593:Grotthuss mechanism
1357:reaction mechanisms
1260:Wade, L.G. (2005).
1160:10.1021/jo00138a007
1124:10.1021/ja01563a037
967:phosphoenolpyruvate
410:Good leaving groups
327:. One example uses
4798:McCormack reaction
4748:Conia-ene reaction
4580:Madelung synthesis
4370:Biginelli reaction
4160:Mumm rearrangement
4045:Favorskii reaction
3980:Cope rearrangement
3970:Chan rearrangement
3735:Rubottom oxidation
3665:Miyaura borylation
3630:Lipid peroxidation
3625:Lindgren oxidation
3605:Kornblum oxidation
3600:Kolbe electrolysis
3545:Fukuyama reduction
3455:Carbonyl reduction
3305:Marker degradation
3167:Diazonium compound
3157:Boudouard reaction
3136:Carbon-heteroatom
3063:Grieco elimination
2849:Rieche formylation
2794:Passerini reaction
2724:Meerwein arylation
2644:Hydroxymethylation
2539:Favorskii reaction
2439:Chan rearrangement
2374:Biginelli reaction
2299:Aldol condensation
2145:2-Norbornyl cation
2120:Möbius aromaticity
2115:Markovnikov's rule
2010:Effective molarity
1955:BĂŒrgiâDunitz angle
1945:Bicycloaromaticity
1758:Arrhenius equation
1528:Oxidative addition
1490:Addition reactions
1241:(11â12): 982â988.
988:Reaction mechanism
963:2-phosphoglycerate
950:
925:Photo-induced E1cB
922:
890:aldol condensation
688:
686:
486:
383:Stepwise reaction
380:Concerted reaction
302:
268:
127:
29:
5090:
5089:
5086:
5085:
5082:
5081:
5074:WohlâAue reaction
4718:6+4 Cycloaddition
4535:Iodolactonization
3855:1,2-rearrangement
3820:WohlâAue reaction
3740:Sabatier reaction
3705:Pinnick oxidation
3670:Mozingo reduction
3615:Leuckart reaction
3570:Haloform reaction
3485:Criegee oxidation
3465:Collins oxidation
3415:Benkeser reaction
3410:Bechamp reduction
3380:Andrussow process
3365:Alcohol oxidation
3275:Edman degradation
3182:Haloform reaction
3131:
3130:
3118:Takai olefination
3083:Julia olefination
2909:Takai olefination
2784:Olefin metathesis
2659:Julia olefination
2584:Grignard reaction
2564:Fukuyama coupling
2479:Coupling reaction
2444:ChanâLam coupling
2314:Alkyne metathesis
2309:Alkane metathesis
2165:Phosphaethynolate
2070:George S. Hammond
2030:Electronic effect
1985:Conjugated system
1867:Stereospecificity
1862:Stereoselectivity
1827:Addition reaction
1816:organic reactions
1781:
1780:
1753:Activated complex
1748:Activation energy
1710:Chemical kinetics
1655:Reaction dynamics
1554:Photodissociation
1299:10.1021/ja0517062
1293:(21): 7698â7699.
1262:Organic Chemistry
1247:10.1002/jlcr.1443
1219:978-1-61583-842-4
1154:(17): 3237â3241.
1089:10.1002/kin.20748
1061:978-1-61583-842-4
1036:978-0-387-95468-4
678:
667:
657:
641:
632:
613:
610:
607:
580:
569:
530:
524:
514:
507:
472:chemical kinetics
446:chemical kinetics
440:Chemical kinetics
431:
430:
377:Stepwise reaction
358:chemical kinetics
16:Chemical reaction
5115:
5069:Wenker synthesis
5059:Stollé synthesis
4914:Bobbitt reaction
4884:Auwers synthesis
4828:Povarov reaction
4753:Cyclopropanation
4691:
4685:Wenker synthesis
4440:Darzens reaction
4390:Bobbitt reaction
4235:Schmidt reaction
4040:Enyne metathesis
3815:Whiting reaction
3810:Wharton reaction
3755:Shapiro reaction
3745:Sarett oxidation
3710:Prévost reaction
3520:Emde degradation
3330:Wohl degradation
3310:Ruff degradation
3280:Emde degradation
3177:Grignard reagent
3113:Shapiro reaction
3098:McMurry reaction
2965:
2929:Ullmann reaction
2894:Stollé synthesis
2884:Stetter reaction
2874:Shapiro reaction
2864:Sakurai reaction
2759:Negishi coupling
2739:Minisci reaction
2734:Michael reaction
2719:McMurry reaction
2714:Mannich reaction
2594:Hammick reaction
2589:Grignard reagent
2529:Enyne metathesis
2514:Doebner reaction
2504:Darzens reaction
2349:Barbier reaction
2339:Auwers synthesis
2266:
2240:Woodward's rules
2205:Superaromaticity
2195:Spiroaromaticity
2095:Inductive effect
2090:Hyperconjugation
2065:Hammett equation
2005:Edwards equation
1857:Regioselectivity
1808:
1801:
1794:
1785:
1685:Collision theory
1634:Matrix isolation
1588:Harpoon reaction
1465:E1cB-elimination
1349:
1342:
1335:
1326:
1319:
1318:
1282:
1276:
1275:
1257:
1251:
1250:
1230:
1224:
1223:
1205:
1199:
1198:
1170:
1164:
1163:
1142:
1136:
1135:
1118:(6): 1406â1412.
1107:
1101:
1100:
1072:
1066:
1065:
1047:
1041:
1040:
1024:
1014:
697:
695:
694:
689:
687:
683:
682:
676:
671:
665:
659:
658:
655:
642:
639:
633:
631:
630:
629:
614:
611:
608:
605:
600:
599:
586:
585:
584:
578:
573:
567:
561:
560:
551:
550:
540:
531:
529:
525:
522:
519:
518:
512:
505:
503:
427:More acidic B-H
363:
251:derivative from
187:, the resulting
133:hydrogen on its
111:transition state
93:molecular entity
5123:
5122:
5118:
5117:
5116:
5114:
5113:
5112:
5093:
5092:
5091:
5078:
4979:Gewald reaction
4862:
4689:
4670:Skraup reaction
4505:Graham reaction
4500:Gewald reaction
4331:
4324:
3846:
3839:
3795:Swern oxidation
3780:Stahl oxidation
3725:Riley oxidation
3680:Omega oxidation
3640:Luche reduction
3590:Jones oxidation
3555:Glycol cleavage
3550:Ganem oxidation
3495:Davis oxidation
3490:Dakin oxidation
3425:Birch reduction
3375:Amide reduction
3341:
3334:
3295:Hooker reaction
3257:
3251:
3139:
3137:
3127:
3123:Wittig reaction
3011:
3007:Wittig reaction
2982:Hooker reaction
2963:
2944:Wittig reaction
2919:Thorpe reaction
2904:Suzuki reaction
2889:Stille reaction
2824:Quelet reaction
2699:Kumada coupling
2649:Ivanov reaction
2639:Hydrovinylation
2619:Hiyama coupling
2579:Glaser coupling
2389:Blaise reaction
2379:Bingel reaction
2364:Benary reaction
2281:
2279:
2273:
2264:
2160:Passive binding
2080:Homoaromaticity
1930:Baldwin's rules
1905:Antiaromaticity
1900:Anomeric effect
1876:
1818:
1812:
1782:
1777:
1763:Eyring equation
1704:
1675:Stereochemistry
1638:
1624:Solvent effects
1612:
1568:
1532:
1513:
1503:
1484:
1479:
1445:
1441:
1422:
1418:
1408:
1398:
1388:
1378:
1359:
1353:
1323:
1322:
1284:
1283:
1279:
1272:
1259:
1258:
1254:
1232:
1231:
1227:
1220:
1207:
1206:
1202:
1172:
1171:
1167:
1144:
1143:
1139:
1109:
1108:
1104:
1074:
1073:
1069:
1062:
1049:
1048:
1044:
1037:
1016:
1015:
1011:
1006:
979:
955:
939:
927:
886:
880:
878:Aldol reactions
871:
855:
847:
840:
833:
826:
822:
816:
807:
800:
793:
782:
777:
771:
762:
756:
752:
747:
739:
735:
730:
722:
718:
713:
685:
684:
650:
643:
635:
634:
621:
588:
587:
552:
542:
541:
532:
520:
504:
493:
492:
468:
462:
442:
436:
421:Less acidic B-H
279:
273:
262:Degradation of
223:eliminating to
119:
17:
12:
11:
5:
5121:
5119:
5111:
5110:
5105:
5095:
5094:
5088:
5087:
5084:
5083:
5080:
5079:
5077:
5076:
5071:
5066:
5061:
5056:
5051:
5046:
5041:
5036:
5031:
5026:
5021:
5016:
5011:
5006:
5001:
4996:
4991:
4986:
4984:Hantzsch ester
4981:
4976:
4971:
4966:
4961:
4956:
4951:
4946:
4941:
4936:
4931:
4926:
4921:
4916:
4911:
4906:
4901:
4896:
4894:Banert cascade
4891:
4886:
4881:
4876:
4870:
4868:
4864:
4863:
4861:
4860:
4855:
4850:
4845:
4840:
4835:
4833:Prato reaction
4830:
4825:
4820:
4815:
4810:
4805:
4800:
4795:
4790:
4785:
4780:
4775:
4770:
4765:
4760:
4755:
4750:
4745:
4740:
4735:
4730:
4725:
4720:
4715:
4710:
4705:
4699:
4697:
4688:
4687:
4682:
4677:
4672:
4667:
4662:
4657:
4652:
4647:
4642:
4637:
4632:
4627:
4622:
4617:
4612:
4607:
4602:
4597:
4592:
4587:
4582:
4577:
4572:
4567:
4562:
4557:
4552:
4547:
4542:
4537:
4532:
4527:
4522:
4517:
4512:
4507:
4502:
4497:
4492:
4487:
4482:
4477:
4472:
4467:
4462:
4457:
4452:
4447:
4442:
4437:
4432:
4427:
4422:
4417:
4412:
4407:
4402:
4397:
4392:
4387:
4382:
4377:
4372:
4367:
4362:
4357:
4352:
4347:
4342:
4336:
4334:
4326:
4325:
4323:
4322:
4317:
4312:
4307:
4302:
4297:
4292:
4287:
4282:
4277:
4272:
4267:
4262:
4257:
4252:
4247:
4242:
4237:
4232:
4227:
4222:
4217:
4212:
4207:
4202:
4197:
4192:
4187:
4182:
4177:
4172:
4167:
4162:
4157:
4152:
4147:
4142:
4137:
4132:
4127:
4122:
4117:
4112:
4107:
4102:
4097:
4092:
4087:
4082:
4077:
4072:
4067:
4062:
4057:
4052:
4047:
4042:
4037:
4032:
4027:
4022:
4017:
4012:
4007:
4002:
3997:
3992:
3987:
3982:
3977:
3972:
3967:
3962:
3957:
3952:
3947:
3942:
3937:
3932:
3927:
3925:Banert cascade
3922:
3917:
3912:
3907:
3902:
3897:
3892:
3887:
3882:
3877:
3872:
3867:
3862:
3857:
3851:
3849:
3845:Rearrangement
3841:
3840:
3838:
3837:
3835:Zinin reaction
3832:
3827:
3822:
3817:
3812:
3807:
3805:Wacker process
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:
3582:
3580:Hydrogenolysis
3577:
3572:
3567:
3562:
3557:
3552:
3547:
3542:
3537:
3532:
3530:Ătard reaction
3527:
3522:
3517:
3512:
3507:
3502:
3497:
3492:
3487:
3482:
3477:
3472:
3467:
3462:
3457:
3452:
3447:
3442:
3437:
3435:Bosch reaction
3432:
3427:
3422:
3417:
3412:
3407:
3402:
3397:
3392:
3387:
3382:
3377:
3372:
3367:
3362:
3357:
3352:
3346:
3344:
3340:Organic redox
3336:
3335:
3333:
3332:
3327:
3322:
3317:
3312:
3307:
3302:
3297:
3292:
3287:
3282:
3277:
3272:
3267:
3261:
3259:
3253:
3252:
3250:
3249:
3244:
3239:
3234:
3229:
3224:
3219:
3214:
3209:
3204:
3199:
3194:
3189:
3184:
3179:
3174:
3172:Esterification
3169:
3164:
3159:
3154:
3149:
3143:
3141:
3133:
3132:
3129:
3128:
3126:
3125:
3120:
3115:
3110:
3105:
3100:
3095:
3090:
3085:
3080:
3075:
3070:
3065:
3060:
3055:
3050:
3045:
3040:
3035:
3030:
3025:
3019:
3017:
3013:
3012:
3010:
3009:
3004:
2999:
2994:
2989:
2984:
2979:
2973:
2971:
2962:
2961:
2956:
2951:
2949:Wurtz reaction
2946:
2941:
2936:
2931:
2926:
2921:
2916:
2911:
2906:
2901:
2896:
2891:
2886:
2881:
2876:
2871:
2866:
2861:
2856:
2851:
2846:
2841:
2836:
2831:
2826:
2821:
2819:Prins reaction
2816:
2811:
2806:
2801:
2796:
2791:
2786:
2781:
2776:
2771:
2766:
2761:
2756:
2751:
2746:
2741:
2736:
2731:
2726:
2721:
2716:
2711:
2706:
2701:
2696:
2691:
2686:
2681:
2676:
2671:
2666:
2661:
2656:
2651:
2646:
2641:
2636:
2634:Hydrocyanation
2631:
2626:
2621:
2616:
2611:
2606:
2604:Henry reaction
2601:
2596:
2591:
2586:
2581:
2576:
2571:
2566:
2561:
2556:
2551:
2546:
2541:
2536:
2531:
2526:
2521:
2516:
2511:
2506:
2501:
2496:
2491:
2486:
2481:
2476:
2471:
2466:
2461:
2456:
2451:
2446:
2441:
2436:
2431:
2426:
2421:
2416:
2411:
2406:
2401:
2396:
2391:
2386:
2381:
2376:
2371:
2366:
2361:
2356:
2351:
2346:
2341:
2336:
2331:
2326:
2321:
2316:
2311:
2306:
2304:Aldol reaction
2301:
2296:
2291:
2285:
2283:
2278:Carbon-carbon
2275:
2274:
2269:
2263:
2262:
2257:
2255:Zaitsev's rule
2252:
2247:
2242:
2237:
2232:
2227:
2222:
2217:
2212:
2207:
2202:
2200:Steric effects
2197:
2192:
2187:
2182:
2177:
2172:
2167:
2162:
2157:
2152:
2147:
2142:
2137:
2132:
2127:
2122:
2117:
2112:
2107:
2102:
2097:
2092:
2087:
2082:
2077:
2072:
2067:
2062:
2057:
2052:
2047:
2042:
2037:
2032:
2027:
2022:
2017:
2012:
2007:
2002:
1997:
1992:
1987:
1982:
1977:
1972:
1967:
1962:
1957:
1952:
1947:
1942:
1937:
1932:
1927:
1922:
1917:
1912:
1907:
1902:
1897:
1892:
1887:
1881:
1878:
1877:
1875:
1874:
1869:
1864:
1859:
1854:
1852:Redox reaction
1849:
1844:
1839:
1837:Polymerization
1834:
1829:
1823:
1820:
1819:
1813:
1811:
1810:
1803:
1796:
1788:
1779:
1778:
1776:
1775:
1770:
1765:
1760:
1755:
1750:
1745:
1740:
1735:
1730:
1725:
1720:
1714:
1712:
1706:
1705:
1703:
1702:
1697:
1692:
1687:
1682:
1677:
1672:
1667:
1662:
1657:
1652:
1646:
1644:
1643:Related topics
1640:
1639:
1637:
1636:
1631:
1626:
1620:
1618:
1617:Medium effects
1614:
1613:
1611:
1610:
1605:
1600:
1595:
1590:
1585:
1579:
1577:
1570:
1569:
1567:
1566:
1561:
1556:
1551:
1546:
1540:
1538:
1534:
1533:
1531:
1530:
1525:
1520:
1515:
1511:
1505:
1501:
1494:
1492:
1486:
1485:
1483:
1482:
1477:
1473:
1467:
1462:
1455:
1453:
1447:
1446:
1444:
1443:
1439:
1432:
1430:
1424:
1423:
1421:
1420:
1416:
1410:
1406:
1400:
1396:
1390:
1386:
1380:
1376:
1369:
1367:
1361:
1360:
1354:
1352:
1351:
1344:
1337:
1329:
1321:
1320:
1277:
1270:
1252:
1225:
1218:
1200:
1165:
1137:
1102:
1083:(2): 118â124.
1067:
1060:
1042:
1035:
1008:
1007:
1005:
1002:
1001:
1000:
995:
990:
985:
978:
975:
954:
951:
937:
926:
923:
906:conjugate base
884:Aldol reaction
882:Main article:
879:
876:
869:
854:
851:
845:
838:
831:
820:
814:
805:
798:
791:
781:
778:
773:Main article:
770:
767:
766:
765:
760:
754:
750:
745:
741:
737:
733:
728:
724:
720:
716:
711:
703:order kinetics
699:
698:
681:
675:
670:
664:
653:
649:
646:
644:
637:
636:
628:
624:
620:
617:
603:
598:
595:
591:
583:
577:
572:
566:
559:
555:
549:
545:
538:
535:
533:
528:
517:
511:
501:
500:
461:
458:
435:
432:
429:
428:
425:
422:
418:
417:
414:
411:
407:
406:
403:
400:
396:
395:
392:
389:
385:
384:
381:
378:
374:
373:
370:
367:
343:, which makes
325:leaving groups
272:
269:
155:delocalization
118:
115:
98:conjugate base
15:
13:
10:
9:
6:
4:
3:
2:
5120:
5109:
5106:
5104:
5101:
5100:
5098:
5075:
5072:
5070:
5067:
5065:
5062:
5060:
5057:
5055:
5052:
5050:
5047:
5045:
5042:
5040:
5037:
5035:
5032:
5030:
5027:
5025:
5022:
5020:
5017:
5015:
5012:
5010:
5007:
5005:
5002:
5000:
4997:
4995:
4994:Herz reaction
4992:
4990:
4987:
4985:
4982:
4980:
4977:
4975:
4972:
4970:
4967:
4965:
4962:
4960:
4957:
4955:
4952:
4950:
4947:
4945:
4942:
4940:
4937:
4935:
4932:
4930:
4927:
4925:
4922:
4920:
4917:
4915:
4912:
4910:
4907:
4905:
4902:
4900:
4897:
4895:
4892:
4890:
4887:
4885:
4882:
4880:
4877:
4875:
4872:
4871:
4869:
4865:
4859:
4856:
4854:
4851:
4849:
4846:
4844:
4841:
4839:
4836:
4834:
4831:
4829:
4826:
4824:
4821:
4819:
4816:
4814:
4811:
4809:
4806:
4804:
4801:
4799:
4796:
4794:
4791:
4789:
4786:
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:
4701:
4700:
4698:
4696:
4695:Cycloaddition
4692:
4686:
4683:
4681:
4678:
4676:
4673:
4671:
4668:
4666:
4663:
4661:
4658:
4656:
4653:
4651:
4648:
4646:
4643:
4641:
4638:
4636:
4633:
4631:
4628:
4626:
4623:
4621:
4618:
4616:
4613:
4611:
4608:
4606:
4603:
4601:
4598:
4596:
4593:
4591:
4588:
4586:
4583:
4581:
4578:
4576:
4573:
4571:
4568:
4566:
4563:
4561:
4558:
4556:
4553:
4551:
4548:
4546:
4543:
4541:
4540:Isay reaction
4538:
4536:
4533:
4531:
4528:
4526:
4523:
4521:
4518:
4516:
4513:
4511:
4508:
4506:
4503:
4501:
4498:
4496:
4493:
4491:
4488:
4486:
4483:
4481:
4478:
4476:
4473:
4471:
4468:
4466:
4463:
4461:
4458:
4456:
4453:
4451:
4448:
4446:
4443:
4441:
4438:
4436:
4435:Cycloaddition
4433:
4431:
4428:
4426:
4423:
4421:
4418:
4416:
4413:
4411:
4408:
4406:
4403:
4401:
4398:
4396:
4393:
4391:
4388:
4386:
4383:
4381:
4378:
4376:
4373:
4371:
4368:
4366:
4363:
4361:
4358:
4356:
4353:
4351:
4348:
4346:
4343:
4341:
4338:
4337:
4335:
4333:
4330:Ring forming
4327:
4321:
4318:
4316:
4313:
4311:
4308:
4306:
4303:
4301:
4298:
4296:
4293:
4291:
4288:
4286:
4283:
4281:
4278:
4276:
4273:
4271:
4268:
4266:
4263:
4261:
4258:
4256:
4253:
4251:
4248:
4246:
4243:
4241:
4238:
4236:
4233:
4231:
4230:Rupe reaction
4228:
4226:
4223:
4221:
4218:
4216:
4213:
4211:
4208:
4206:
4203:
4201:
4198:
4196:
4193:
4191:
4188:
4186:
4183:
4181:
4178:
4176:
4173:
4171:
4168:
4166:
4163:
4161:
4158:
4156:
4153:
4151:
4148:
4146:
4143:
4141:
4138:
4136:
4133:
4131:
4128:
4126:
4123:
4121:
4118:
4116:
4113:
4111:
4108:
4106:
4103:
4101:
4098:
4096:
4093:
4091:
4088:
4086:
4083:
4081:
4078:
4076:
4073:
4071:
4068:
4066:
4063:
4061:
4058:
4056:
4053:
4051:
4048:
4046:
4043:
4041:
4038:
4036:
4033:
4031:
4028:
4026:
4023:
4021:
4018:
4016:
4013:
4011:
4008:
4006:
4003:
4001:
3998:
3996:
3993:
3991:
3988:
3986:
3983:
3981:
3978:
3976:
3973:
3971:
3968:
3966:
3963:
3961:
3958:
3956:
3953:
3951:
3948:
3946:
3943:
3941:
3938:
3936:
3933:
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:
3852:
3850:
3848:
3842:
3836:
3833:
3831:
3828:
3826:
3823:
3821:
3818:
3816:
3813:
3811:
3808:
3806:
3803:
3801:
3798:
3796:
3793:
3791:
3788:
3786:
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:
3678:
3676:
3673:
3671:
3668:
3666:
3663:
3661:
3658:
3656:
3653:
3651:
3648:
3646:
3643:
3641:
3638:
3636:
3633:
3631:
3628:
3626:
3623:
3621:
3620:Ley oxidation
3618:
3616:
3613:
3611:
3608:
3606:
3603:
3601:
3598:
3596:
3593:
3591:
3588:
3586:
3585:Hydroxylation
3583:
3581:
3578:
3576:
3575:Hydrogenation
3573:
3571:
3568:
3566:
3563:
3561:
3558:
3556:
3553:
3551:
3548:
3546:
3543:
3541:
3538:
3536:
3533:
3531:
3528:
3526:
3523:
3521:
3518:
3516:
3513:
3511:
3510:DNA oxidation
3508:
3506:
3503:
3501:
3500:Deoxygenation
3498:
3496:
3493:
3491:
3488:
3486:
3483:
3481:
3478:
3476:
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:
3390:Aromatization
3388:
3386:
3383:
3381:
3378:
3376:
3373:
3371:
3368:
3366:
3363:
3361:
3358:
3356:
3353:
3351:
3348:
3347:
3345:
3343:
3337:
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:
3262:
3260:
3254:
3248:
3245:
3243:
3240:
3238:
3235:
3233:
3230:
3228:
3227:Reed reaction
3225:
3223:
3220:
3218:
3215:
3213:
3210:
3208:
3205:
3203:
3200:
3198:
3195:
3193:
3190:
3188:
3185:
3183:
3180:
3178:
3175:
3173:
3170:
3168:
3165:
3163:
3160:
3158:
3155:
3153:
3150:
3148:
3145:
3144:
3142:
3138:bond forming
3134:
3124:
3121:
3119:
3116:
3114:
3111:
3109:
3106:
3104:
3101:
3099:
3096:
3094:
3091:
3089:
3086:
3084:
3081:
3079:
3076:
3074:
3071:
3069:
3066:
3064:
3061:
3059:
3056:
3054:
3051:
3049:
3046:
3044:
3043:Cope reaction
3041:
3039:
3036:
3034:
3031:
3029:
3026:
3024:
3021:
3020:
3018:
3014:
3008:
3005:
3003:
3000:
2998:
2995:
2993:
2990:
2988:
2985:
2983:
2980:
2978:
2975:
2974:
2972:
2970:
2966:
2960:
2957:
2955:
2952:
2950:
2947:
2945:
2942:
2940:
2937:
2935:
2932:
2930:
2927:
2925:
2922:
2920:
2917:
2915:
2912:
2910:
2907:
2905:
2902:
2900:
2897:
2895:
2892:
2890:
2887:
2885:
2882:
2880:
2877:
2875:
2872:
2870:
2867:
2865:
2862:
2860:
2857:
2855:
2852:
2850:
2847:
2845:
2842:
2840:
2837:
2835:
2832:
2830:
2827:
2825:
2822:
2820:
2817:
2815:
2812:
2810:
2807:
2805:
2802:
2800:
2797:
2795:
2792:
2790:
2787:
2785:
2782:
2780:
2777:
2775:
2772:
2770:
2767:
2765:
2762:
2760:
2757:
2755:
2754:Nef synthesis
2752:
2750:
2747:
2745:
2742:
2740:
2737:
2735:
2732:
2730:
2729:Methylenation
2727:
2725:
2722:
2720:
2717:
2715:
2712:
2710:
2707:
2705:
2702:
2700:
2697:
2695:
2692:
2690:
2687:
2685:
2682:
2680:
2677:
2675:
2672:
2670:
2667:
2665:
2662:
2660:
2657:
2655:
2652:
2650:
2647:
2645:
2642:
2640:
2637:
2635:
2632:
2630:
2627:
2625:
2622:
2620:
2617:
2615:
2612:
2610:
2607:
2605:
2602:
2600:
2599:Heck reaction
2597:
2595:
2592:
2590:
2587:
2585:
2582:
2580:
2577:
2575:
2572:
2570:
2567:
2565:
2562:
2560:
2557:
2555:
2552:
2550:
2547:
2545:
2542:
2540:
2537:
2535:
2532:
2530:
2527:
2525:
2522:
2520:
2517:
2515:
2512:
2510:
2507:
2505:
2502:
2500:
2497:
2495:
2492:
2490:
2487:
2485:
2482:
2480:
2477:
2475:
2472:
2470:
2467:
2465:
2462:
2460:
2457:
2455:
2452:
2450:
2447:
2445:
2442:
2440:
2437:
2435:
2432:
2430:
2427:
2425:
2422:
2420:
2417:
2415:
2412:
2410:
2407:
2405:
2402:
2400:
2397:
2395:
2392:
2390:
2387:
2385:
2382:
2380:
2377:
2375:
2372:
2370:
2367:
2365:
2362:
2360:
2357:
2355:
2352:
2350:
2347:
2345:
2342:
2340:
2337:
2335:
2332:
2330:
2327:
2325:
2322:
2320:
2317:
2315:
2312:
2310:
2307:
2305:
2302:
2300:
2297:
2295:
2292:
2290:
2287:
2286:
2284:
2280:bond forming
2276:
2272:
2267:
2261:
2258:
2256:
2253:
2251:
2248:
2246:
2245:Y-aromaticity
2243:
2241:
2238:
2236:
2233:
2231:
2230:Walsh diagram
2228:
2226:
2223:
2221:
2218:
2216:
2215:Taft equation
2213:
2211:
2208:
2206:
2203:
2201:
2198:
2196:
2193:
2191:
2188:
2186:
2185:ÎŁ-aromaticity
2183:
2181:
2178:
2176:
2173:
2171:
2168:
2166:
2163:
2161:
2158:
2156:
2153:
2151:
2148:
2146:
2143:
2141:
2138:
2136:
2133:
2131:
2128:
2126:
2123:
2121:
2118:
2116:
2113:
2111:
2110:Marcus theory
2108:
2106:
2103:
2101:
2098:
2096:
2093:
2091:
2088:
2086:
2085:HĂŒckel's rule
2083:
2081:
2078:
2076:
2073:
2071:
2068:
2066:
2063:
2061:
2058:
2056:
2053:
2051:
2048:
2046:
2043:
2041:
2040:Evelyn effect
2038:
2036:
2033:
2031:
2028:
2026:
2023:
2021:
2020:Electron-rich
2018:
2016:
2013:
2011:
2008:
2006:
2003:
2001:
1998:
1996:
1993:
1991:
1988:
1986:
1983:
1981:
1978:
1976:
1973:
1971:
1968:
1966:
1963:
1961:
1958:
1956:
1953:
1951:
1948:
1946:
1943:
1941:
1938:
1936:
1935:Bema Hapothle
1933:
1931:
1928:
1926:
1923:
1921:
1918:
1916:
1913:
1911:
1908:
1906:
1903:
1901:
1898:
1896:
1893:
1891:
1888:
1886:
1883:
1882:
1879:
1873:
1870:
1868:
1865:
1863:
1860:
1858:
1855:
1853:
1850:
1848:
1845:
1843:
1840:
1838:
1835:
1833:
1830:
1828:
1825:
1824:
1821:
1817:
1809:
1804:
1802:
1797:
1795:
1790:
1789:
1786:
1774:
1771:
1769:
1766:
1764:
1761:
1759:
1756:
1754:
1751:
1749:
1746:
1744:
1741:
1739:
1736:
1734:
1731:
1729:
1726:
1724:
1721:
1719:
1718:Rate equation
1716:
1715:
1713:
1711:
1707:
1701:
1698:
1696:
1693:
1691:
1690:Arrow pushing
1688:
1686:
1683:
1681:
1678:
1676:
1673:
1671:
1668:
1666:
1663:
1661:
1658:
1656:
1653:
1651:
1648:
1647:
1645:
1641:
1635:
1632:
1630:
1627:
1625:
1622:
1621:
1619:
1615:
1609:
1606:
1604:
1601:
1599:
1598:Marcus theory
1596:
1594:
1591:
1589:
1586:
1584:
1581:
1580:
1578:
1575:
1571:
1565:
1562:
1560:
1557:
1555:
1552:
1550:
1549:Isomerization
1547:
1545:
1542:
1541:
1539:
1535:
1529:
1526:
1524:
1523:Cycloaddition
1521:
1519:
1516:
1509:
1506:
1499:
1496:
1495:
1493:
1491:
1487:
1481:
1474:
1471:
1468:
1466:
1463:
1460:
1457:
1456:
1454:
1452:
1448:
1437:
1434:
1433:
1431:
1429:
1425:
1414:
1411:
1404:
1401:
1394:
1391:
1384:
1381:
1374:
1371:
1370:
1368:
1366:
1362:
1358:
1350:
1345:
1343:
1338:
1336:
1331:
1330:
1327:
1316:
1312:
1308:
1304:
1300:
1296:
1292:
1288:
1281:
1278:
1273:
1271:0-13-236731-9
1267:
1263:
1256:
1253:
1248:
1244:
1240:
1236:
1229:
1226:
1221:
1215:
1211:
1204:
1201:
1196:
1192:
1188:
1184:
1180:
1176:
1169:
1166:
1161:
1157:
1153:
1149:
1141:
1138:
1133:
1129:
1125:
1121:
1117:
1113:
1106:
1103:
1098:
1094:
1090:
1086:
1082:
1078:
1071:
1068:
1063:
1057:
1053:
1046:
1043:
1038:
1032:
1028:
1023:
1022:
1013:
1010:
1003:
999:
996:
994:
991:
989:
986:
984:
981:
980:
976:
974:
972:
968:
964:
960:
952:
946:
942:
940:
932:
924:
918:
914:
912:
907:
903:
899:
895:
894:deprotonation
891:
885:
877:
875:
872:
864:
860:
852:
850:
848:
841:
834:
823:
812:
808:
801:
794:
787:
779:
776:
768:
763:
748:
742:
731:
725:
714:
708:
707:
706:
704:
651:
647:
645:
626:
622:
618:
596:
593:
589:
557:
553:
547:
543:
536:
534:
526:
491:
490:
489:
482:
478:
475:
473:
467:
466:Rate equation
459:
457:
455:
451:
447:
441:
433:
426:
423:
420:
419:
415:
413:Leaving group
412:
409:
408:
404:
402:No preference
401:
398:
397:
393:
390:
387:
386:
382:
379:
376:
375:
371:
368:
365:
364:
361:
359:
354:
350:
349:leaving group
346:
342:
338:
334:
330:
326:
323:
319:
316:
312:
307:
298:
294:
292:
288:
284:
278:
270:
265:
260:
256:
254:
250:
246:
242:
238:
234:
230:
227:than from an
226:
222:
218:
217:fluoroalkanes
214:
210:
206:
202:
201:leaving group
198:
194:
190:
186:
182:
178:
175:
171:
167:
163:
160:
156:
152:
148:
144:
140:
139:leaving group
136:
132:
123:
116:
114:
112:
106:
104:
100:
99:
94:
90:
86:
82:
78:
74:
70:
66:
63:- stands for
62:
58:
54:
50:
46:
42:
41:leaving group
38:
35:is a type of
34:
26:
21:
4035:Ene reaction
3395:Autoxidation
3256:Degradation
3147:Azo coupling
2924:Ugi reaction
2524:Ene reaction
2324:Alkynylation
2175:Polyfluorene
2170:Polar effect
2035:Electrophile
1950:Bredt's rule
1920:Baird's rule
1890:Alpha effect
1670:Molecularity
1464:
1290:
1286:
1280:
1261:
1255:
1238:
1234:
1228:
1209:
1203:
1178:
1174:
1168:
1151:
1147:
1140:
1115:
1111:
1105:
1080:
1076:
1070:
1051:
1045:
1020:
1012:
956:
935:
930:
928:
887:
867:
856:
843:
836:
829:
818:
803:
796:
789:
783:
758:
743:
726:
709:
700:
487:
476:
469:
443:
318:intermediate
303:
283:substituents
280:
264:ethiofencarb
253:ethiofencarb
237:carbon-based
170:ethiofencarb
128:
107:
103:intermediate
96:
89:Unimolecular
88:
80:
76:
72:
71:nimolecular
68:
64:
60:
32:
30:
2534:Ethenolysis
2180:Ring strain
2150:Nucleophile
1975:Clar's rule
1915:Aromaticity
1629:Cage effect
1564:RRKM theory
1480:elimination
993:Carbocation
241:heteroatoms
177:insecticide
95:. Finally,
81:Elimination
67:limination
57:triple bond
5097:Categories
4818:Ozonolysis
4345:Annulation
3695:Ozonolysis
1814:Topics in
1181:(4): 490.
1004:References
959:glycolysis
953:In biology
464:See also:
438:See also:
424:Acidic B-H
275:See also:
243:, such as
205:ionization
193:conjugated
4332:reactions
3847:reactions
3342:reactions
3258:reactions
3140:reactions
2282:reactions
1680:Catalysis
1576:reactions
1307:0002-7863
1195:0009-2681
1132:0002-7863
1097:0538-8066
998:Carbanion
825:material.
811:deuterium
780:Deuterium
666:substrate
606:conjugate
594:−
568:substrate
450:rate laws
315:carbanion
306:concerted
181:half-life
174:carbamate
166:resonance
162:lone pair
151:induction
143:α- carbon
117:Mechanism
75:onjugate
25:hemiketal
2225:Vinylogy
1895:Annulene
1842:Reagents
1315:15913358
977:See also
898:carbonyl
859:Fluorine
460:Rate law
452:and the
345:fluorine
341:fluorine
335:for the
329:chlorine
287:carbonyl
245:nitrogen
213:alcohols
197:carbonyl
164:through
159:electron
135:ÎČ-carbon
1885:A value
971:enolase
902:enolate
333:halogen
322:halogen
225:alkynes
221:alkenes
157:of the
147:anionic
141:on the
1355:Basic
1313:
1305:
1268:
1216:
1193:
1130:
1095:
1058:
1033:
931:et al.
802:, and
609:
249:phenol
229:alkane
131:acidic
53:double
1583:Redox
1419:Acyl)
1027:53â56
839:anion
799:anion
761:anion
712:anion
372:E1cB
339:than
337:anion
291:cyano
189:amide
185:amine
79:ase.
49:anion
1472:(E2)
1461:(E1)
1311:PMID
1303:ISSN
1266:ISBN
1214:ISBN
1191:ISSN
1128:ISSN
1093:ISSN
1056:ISBN
1031:ISBN
936:E1cB
868:E1cB
844:E1cB
837:E1cB
830:E1cB
819:E1cB
804:E1cB
797:E1cB
790:E1cB
759:E1cB
744:E1cB
727:E1cB
710:E1cB
677:base
640:rate
612:acid
579:base
347:the
289:and
215:and
172:- a
61:E1cB
45:base
31:The
1442:Ar)
1399:Ar)
1295:doi
1291:127
1243:doi
1183:doi
1156:doi
1120:doi
1085:doi
965:to
938:irr
870:irr
846:rev
832:irr
821:rev
806:irr
792:rev
753:â« k
746:irr
736:â« k
729:rev
719:â« k
656:obs
153:or
55:or
5099::
1510:(A
1500:(A
1438:(S
1415:(S
1409:i)
1405:(S
1395:(S
1389:2)
1385:(S
1379:1)
1375:(S
1309:.
1301:.
1289:.
1239:50
1237:.
1189:.
1179:21
1177:.
1152:47
1150:.
1126:.
1116:79
1114:.
1091:.
1081:45
1079:.
1029:.
973:.
941:.
849:.
795:,
755:â1
740:).
734:â1
723:).
369:E2
366:E1
360:.
353:E2
311:E2
255:.
233:sp
209:E2
1807:e
1800:t
1793:v
1514:)
1512:N
1504:)
1502:E
1478:i
1476:E
1440:E
1417:N
1407:N
1397:N
1387:N
1377:N
1348:e
1341:t
1334:v
1317:.
1297::
1274:.
1249:.
1245::
1222:.
1197:.
1185::
1162:.
1158::
1134:.
1122::
1099:.
1087::
1064:.
1039:.
815:3
751:2
738:2
721:2
717:1
680:]
674:[
669:]
663:[
652:k
648:=
627:2
623:k
619:+
616:]
602:[
597:1
590:k
582:]
576:[
571:]
565:[
558:2
554:k
548:1
544:k
537:=
527:t
523:d
516:]
513:P
510:[
506:d
77:B
73:c
69:U
65:E
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