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, Deviation: ±0.11 |
|
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, Deviation: ±0.96 |
|
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, Deviation: ±0.21 |
|
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 |