C-Electrophiles
| Name | Solvent |
Reactivity Parameters |
Classification |
Reference (title or year) |
|---|---|---|---|---|
p-(dimethylamino)benzylidene Meldrum's acid![]() ![]() |
E Param.: -12.76 | J. Org. Chem. 2008, 73, 2738-2745 10.1021/jo702590s | ||
4-cyano-<i>trans-beta</i>-nitrostyrene![]() ![]() |
E Param.: -12.61 | J. Org. Chem. 2011, 76, 9370-9378 10.1021/jo201678u | ||
4-nitro-<i>trans-beta</i>-nitrostyrene![]() ![]() |
E Param.: -12.37 | J. Org. Chem. 2011, 76, 9370-9378 10.1021/jo201678u | ||
2,4-dinitrothiophene![]() ![]() |
E Param.: -12.33 | J. Org. Chem. 2005, 70, 6242-6253 10.1021/jo0505526 | ||
2,5-dichloroquinone (C-H)![]() ![]() |
E Param.: -12.28 | J. Am. Chem. Soc. 2014, 136, 11499-11512 10.1021/ja505613b | ||
ani(Ph)2QM![]() ![]() |
E Param.: -12.18 | Angew. Chem. Int. Ed. 2002, 41, 91-95 10.1002/1521-3773(20[...] | ||
p-chloranil (C=O)![]() ![]() |
E Param.: -12.13 | J. Am. Chem. Soc. 2014, 136, 11499-11512 10.1021/ja505613b | ||
ethenesulfonyl fluoride (ESF)![]() ![]() |
DMSO | E Param.: -12.09 | Angew. Chem. Int. Ed. 2016, 55, 12664-12667 10.1002/anie.201601875 | |
o-chloranil (C-Cl)![]() ![]() |
E Param.: -12.02 | J. Am. Chem. Soc. 2014, 136, 11499-11512 10.1021/ja505613b | ||
2-cinnamoyl-1-(2,6-dimethoxyphenyl)-3-methyl-1H-imidazol-3-ium![]() ![]() |
DMSO | E Param.: -12.02 | Top. Catal. 2018, 61, 585-590 10.1007/s11244-018-0[...] | |
ethyl 2-(3,5-di-tert-butyl-4-oxocyclohexa-2,5-dien-1-ylidene)acetate![]() ![]() |
E Param.: -12.01 | Chem. Eur. J. 2025, 31, e202501224 10.1002/chem.202501224 | ||
jul(S)BBS![]() ![]() |
E Param.: -11.89 | J. Org. Chem. 2007, 72, 9170-9180 10.1021/jo071273g | ||
2-(3,5-di-tert-butyl-4-oxocyclohexa-2,5-dien-1-ylidene)acetonitrile![]() ![]() |
E Param.: -11.88 | Chem. Eur. J. 2025, 31, e202501224 10.1002/chem.202501224 | ||
2,6-diphenyl-4-benzylidenecyclohexa-2,5-dienone![]() ![]() |
E Param.: -11.87 | Eur. J. Org. Chem. 2009, , 3203-3211 10.1002/ejoc.200900299 | ||
1-(tert-butyl)-2-cinnamoyl-3-methyl-1H-imidazol-3-ium![]() ![]() |
DMSO | E Param.: -11.80 | Top. Catal. 2018, 61, 585-590 10.1007/s11244-018-0[...] | |
2-cinnamoyl-1-(4-methoxyphenyl)-3-methyl-1H-imidazol-3-ium![]() ![]() |
DMSO | E Param.: -11.79 | Top. Catal. 2018, 61, 585-590 10.1007/s11244-018-0[...] | |
2-benzylidenebenzo[d][1,3]dithiole 1,1,3,3-tetraoxide![]() ![]() |
DMSO | E Param.: -11.78 | Chem. Asian J. 2012, 7, 1401-1407 10.1002/asia.201101046 | |
2,6-di-tert-butyl-4-(2,2,2-trifluoroethylidene)cyclohexa-2,5-dien-1-one![]() ![]() |
DMSO | E Param.: -11.68 | Eur. J. Org. Chem. 2020, , 3812-3817 10.1002/ejoc.202000295 | |
2-cinnamoyl-1,3-dimethyl-1H-imidazol-3-ium![]() ![]() |
DMSO | E Param.: -11.52 | Angew. Chem. Int. Ed. 2012, 51, 5234-5238 10.1002/anie.201109042 | |
(E)-N-benzylidene-4-methylbenzenesulfonamide (in DMSO)![]() ![]() |
DMSO | E Param.: -11.50 | J. Am. Chem. Soc. 2011, 133, 8240-8251 10.1021/ja200820m | |
2-cinnamoyl-1-mesityl-3-methyl-1H-imidazol-3-ium![]() ![]() |
DMSO | E Param.: -11.48 | Top. Catal. 2018, 61, 585-590 10.1007/s11244-018-0[...] | |
2-(p-methoxybenzylidene)-indan-1,3-dione![]() ![]() |
E Param.: -11.32 | Org. Biomol. Chem. 2007, 5, 3020-3026 10.1039/b708025e | ||
maleic anhydride![]() ![]() |
DMSO | E Param.: -11.31 | Eur. J. Org. Chem. 2014, , 2956-2963 10.1002/ejoc.201301779 | |
(4-NMe2)3-tritylium ion (= Crystal violet)![]() ![]() |
E Param.: -11.26 | J. Am. Chem. Soc. 2003, 125, 286-295 10.1021/ja021010y | ||
dicarbonyl(cyclopentadienyl)propene-iron(II)![]() ![]() |
E Param.: -11.20 | Helv. Chim. Acta 2005, 88, 1754-1768 10.1002/hlca.200590137 | ||
2,6-di-tert-butyl-4-methylenecyclohexa-2,5-dien-1-one![]() ![]() |
E Param.: -11.17 | Chem. Eur. J. 2025, 31, e202501224 10.1002/chem.202501224 | ||
p-fluoranil (C-F)![]() ![]() |
E Param.: -11.12 | J. Am. Chem. Soc. 2014, 136, 11499-11512 10.1021/ja505613b | ||
p-(methoxy)benzylidenemalononitrile![]() ![]() |
E Param.: -10.80 | J. Org. Chem. 2003, 68, 6880-6886 10.1021/jo0344182 | ||
dma(S)BBS![]() ![]() |
E Param.: -10.73 | J. Org. Chem. 2007, 72, 9170-9180 10.1021/jo071273g | ||
p-AniCH=N+Me2 (in MeCN)![]() ![]() |
MeCN | E Param.: -10.69 | J. Am. Chem. Soc. 2013, 135, 6579-6587 10.1021/ja401106x | |
(S,E)-5-benzyl-1-((E)-3-(4-(dimethylamino)phenyl)allylidene)-2,2,3-trimethyl-4-oxoimidazolidin-1-ium![]() ![]() |
dichloromethane | E Param.: -10.60 | Asian J. Org. Chem. 2014, 3, 550-555 10.1002/ajoc.201402009 | |
aniBBS![]() ![]() |
E Param.: -10.37 | J. Org. Chem. 2007, 72, 9170-9180 10.1021/jo071273g | ||
pipN+=CH-CH-Ph![]() ![]() |
E Param.: -10.30 | Angew. Chem. Int. Ed. 2008, 47, 8723-8726 10.1002/anie.200802889 | ||
(4-NMe2)2-tritylium ion (= Malachite green)![]() ![]() |
E Param.: -10.29 | J. Am. Chem. Soc. 2003, 125, 286-295 10.1021/ja021010y | ||
p-(methoxy)benzylidene Meldrum's acid![]() ![]() |
E Param.: -10.28 | J. Org. Chem. 2008, 73, 2738-2745 10.1021/jo702590s | ||
bis(1,2-dimethylindol-3-yl)methylium ion![]() ![]() |
E Param.: -10.23 | J. Org. Chem. 2015, 80, 8643-8656 10.1021/acs.joc.5b01298 | ||
Pd-allyl cation![]() ![]() |
E Param.: -10.11 | Acc. Chem. Res. 2003, 36, 66-77 10.1021/ar020094c | ||
2-benzylidene-indan-1,3-dione![]() ![]() |
E Param.: -10.11 | Org. Biomol. Chem. 2007, 5, 3020-3026 10.1039/b708025e | ||
2-cinnamoyl-3-methyl-1-(perfluorophenyl)-1H-imidazol-3-ium![]() ![]() |
DMSO | E Param.: -10.09 | Top. Catal. 2018, 61, 585-590 10.1007/s11244-018-0[...] | |
(lil)2CH+![]() ![]() |
E Param.: -10.04 | J. Am. Chem. Soc. 2001, 123, 9500-9512 10.1021/ja010890y | ||
1,1,3-tris(4-(dimethylamino)phenyl)allylium ion![]() ![]() |
E Param.: -9.84 | Acc. Chem. Res. 2003, 36, 66-77 10.1021/ar020094c | ||
pyrN+=CH-CH-Ph![]() ![]() |
E Param.: -9.80 | Angew. Chem. Int. Ed. 2008, 47, 8723-8726 10.1002/anie.200802889 | ||
bis(julidin-9-yl)allylium ion![]() ![]() |
E Param.: -9.78 | J. Org. Chem. 2011, 76, 9391-9408 10.1021/jo201668w | ||
pTolCH=N+CH2 (in MeCN)![]() ![]() |
MeCN | E Param.: -9.64 | J. Am. Chem. Soc. 2013, 135, 6579-6587 10.1021/ja401106x | |
PhCH=N+(CH2)5 (in MeCN)![]() ![]() |
MeCN | E Param.: -9.60 | J. Am. Chem. Soc. 2013, 135, 6579-6587 10.1021/ja401106x | |
indolecarboxylate derived iminium ion![]() ![]() |
dichloromethane | E Param.: -9.50 | Angew. Chem. Int. Ed. 2009, 48, 5034-5037 10.1002/anie.200900933 | |
(jul)2CH+![]() ![]() |
E Param.: -9.45 | J. Am. Chem. Soc. 2001, 123, 9500-9512 10.1021/ja010890y | ||
benzylidenemalononitrile![]() ![]() |
E Param.: -9.42 | J. Org. Chem. 2003, 68, 6880-6886 10.1021/jo0344182 | ||
p-fluoranil (C=O)![]() ![]() |
E Param.: -9.37 | J. Am. Chem. Soc. 2014, 136, 11499-11512 10.1021/ja505613b | ||
PhCH=N+(CH2)4 (in MeCN)![]() ![]() |
MeCN | E Param.: -9.35 | J. Am. Chem. Soc. 2013, 135, 6579-6587 10.1021/ja401106x |



















































