C-Electrophiles
| Name | Solvent |
Reactivity Parameters |
Classification |
Reference (title or year) |
|---|---|---|---|---|
PhCH=N+Me2 (in MeCN)   |
MeCN | E Param.: -9.27 |
 |
J. Am. Chem. Soc. 2013, 135, 6579-6587 10.1021/ja401106x |
C7H9+-Fe(CO)3  |
E Param.: -9.21, Deviation: ±0.36 |
|
Acc. Chem. Res. 2003, 36, 66-77 10.1021/ar020094c |
|
Me2N+=CH-CH-Ph  |
E Param.: -9.20 |
|
Angew. Chem. Int. Ed. 2008, 47, 8723-8726 10.1002/anie.200802889 |
|
benzylidene-Meldrum's acid  |
E Param.: -9.15 |
|
J. Org. Chem. 2008, 73, 2738-2745 10.1021/jo702590s |
|
6-nitro-tetrazolo[1,5a]pyridine  |
E Param.: -9.05, Deviation: ±0.12 |
|
J. Org. Chem. 2005, 70, 6242-6253 10.1021/jo0505526 |
|
1,1-bis(4-dimethylaminophenyl)-3-phenylallylium ion  |
E Param.: -8.97, Deviation: ±0.32 |
|
Acc. Chem. Res. 2003, 36, 66-77 10.1021/ar020094c |
|
C6H6OMe+-Fe(CO)3  |
E Param.: -8.94, Deviation: ±0.13 |
|
Acc. Chem. Res. 2003, 36, 66-77 10.1021/ar020094c |
|
o-chloranil (C=O)  |
E Param.: -8.77 |
|
J. Am. Chem. Soc. 2014, 136, 11499-11512 10.1021/ja505613b |
|
(ind)2CH+  |
E Param.: -8.76 |
|
J. Am. Chem. Soc. 2001, 123, 9500-9512 10.1021/ja010890y |
|
ani(Br)2QM  |
E Param.: -8.63 |
|
Angew. Chem. Int. Ed. 2002, 41, 91-95 10.1002/1521-3773(20[...] |
|
mor iminium  |
E Param.: -8.60 |
|
Angew. Chem. Int. Ed. 2008, 47, 8723-8726 10.1002/anie.200802889 |
|
fc2CH+  |
E Param.: -8.54, Deviation: ±0.53 |
|
Acc. Chem. Res. 2003, 36, 66-77 10.1021/ar020094c |
|
(PhCH2)2N+=CH-CH-Ph  |
E Param.: -8.50 |
|
Angew. Chem. Int. Ed. 2008, 47, 8723-8726 10.1002/anie.200802889 |
|
5-methoxyfuroxano[3,4-d]pyrimidine  |
E Param.: -8.37 |
|
J. Phys. Org. Chem. 2003, 16, 431-437 10.1002/poc.606 |
|
p-CF3-C6H4-CH=N+Me2 (in MeCN)  |
MeCN | E Param.: -8.34 |
|
J. Am. Chem. Soc. 2013, 135, 6579-6587 10.1021/ja401106x |
(thq)2CH+  |
E Param.: -8.22 |
|
J. Am. Chem. Soc. 2001, 123, 9500-9512 10.1021/ja010890y |
|
Jorgensen/Hayashi-iminium ion  |
E Param.: -8.20 |
|
Angew. Chem. Int. Ed. 2008, 47, 8723-8726 10.1002/anie.200802889 |
|
(S,E)-5-benzyl-1-((E)-3-(4-methoxyphenyl)allylidene)-2,2,3-trimethyl-4-oxoimidazolidin-1-ium  |
dichloromethane | E Param.: -8.00 |
|
Asian J. Org. Chem. 2014, 3, 550-555 10.1002/ajoc.201402009 |
(4-NMe2)-tritylium ion  |
E Param.: -7.93 |
 |
J. Am. Chem. Soc. 2003, 125, 286-295 10.1021/ja021010y |
|
1-methyl-3-((julolidin-9-yl)methylene)-3H-indol-1-ium ion  |
E Param.: -7.79 |
|
J. Org. Chem. 2015, 80, 8643-8656 10.1021/acs.joc.5b01298 |
|
C6H7+-Fe(CO)3  |
E Param.: -7.76, Deviation: ±0.31 |
|
Acc. Chem. Res. 2003, 36, 66-77 10.1021/ar020094c |
|
(pyr)2CH+  |
E Param.: -7.69 |
|
J. Am. Chem. Soc. 2001, 123, 9500-9512 10.1021/ja010890y |
|
p-tosyl isocyanate  |
MeCN | E Param.: -7.69 |
|
J. Am. Chem. Soc. 2020, 142, 8383-8402 10.1021/jacs.0c01960 |
MacMillan-iminium ion (spiro)  |
MeCN | E Param.: -7.67 |
|
Angew. Chem. Int. Ed. 2011, 50, 9953-9956 10.1002/anie.201103683 |
diarylallylium ion (4-NMe2)2  |
E Param.: -7.50 |
|
J. Org. Chem. 2011, 76, 9391-9408 10.1021/jo201668w |
|
(ethene-1,1-diyldisulfonyl)dibenzene  |
DMSO | E Param.: -7.50 |
|
Chem. Asian J. 2012, 7, 1401-1407 10.1002/asia.201101046 |
MacMillan-iminium ion (1st generation)  |
MeCN | E Param.: -7.37 |
|
Angew. Chem. Int. Ed. 2011, 50, 9953-9956 10.1002/anie.201103683 |
(S,E)-5-((1H-indol-3-yl)methyl)-2,2,3-trimethyl-4-oxo-1-((E)-3-phenylallylidene)imidazolidin-1-ium  |
dichloromethane | E Param.: -7.30 |
|
Asian J. Org. Chem. 2014, 3, 550-555 10.1002/ajoc.201402009 |
(S,E)-5-benzyl-2,2,3-trimethyl-4-oxo-1-((E)-3-(p-tolyl)allylidene)imidazolidin-1-ium  |
dichloromethane | E Param.: -7.20 |
|
Asian J. Org. Chem. 2014, 3, 550-555 10.1002/ajoc.201402009 |
N-methylacridinium ion  |
E Param.: -7.15, Deviation: ±0.12 |
|
Acc. Chem. Res. 2003, 36, 66-77 10.1021/ar020094c |
|
(dma)2CH+  |
E Param.: -7.02 |
|
J. Am. Chem. Soc. 2001, 123, 9500-9512 10.1021/ja010890y |
|
6-cyano-4-nitrobenzofuroxan  |
E Param.: -7.01, Deviation: ±0.16 |
|
J. Org. Chem. 2005, 70, 6242-6253 10.1021/jo0505526 |
|
(S,E)-2,2,3-trimethyl-4-oxo-1-((E)-3-phenylallylidene)-5-(3,4,5-trimethoxybenzyl)imidazolidin-1-ium  |
dichloromethane | E Param.: -7.00 |
|
Angew. Chem. Int. Ed. 2013, 52, 7967-7971 10.1002/anie.201301864 |
bis(5-methoxy-1-methylindol-3-yl)methylium ion  |
E Param.: -6.90 |
|
J. Org. Chem. 2015, 80, 8643-8656 10.1021/acs.joc.5b01298 |
|
dimethylmethyleneammonium ion  |
E Param.: -6.69 |
|
Acc. Chem. Res. 2003, 36, 66-77 10.1021/ar020094c |
|
2-phenyl-1,3-dithianylium ion  |
E Param.: -6.43, Deviation: ±0.04 |
|
Acc. Chem. Res. 2003, 36, 66-77 10.1021/ar020094c |
|
4-cyano-6-nitro-benzofuroxane  |
E Param.: -6.41, Deviation: ±0.38 |
|
J. Org. Chem. 2005, 70, 6242-6253 10.1021/jo0505526 |
|
3-(4-(dimethylamino)benzylidene)-1-methyl-3H-indol-1-ium ion  |
E Param.: -6.26 |
|
J. Org. Chem. 2015, 80, 8643-8656 10.1021/acs.joc.5b01298 |
|
1-phenyl-propyn-1-ylium-Co2(CO)5(PPh3)  |
E Param.: -6.19, Deviation: ±0.44 |
|
Acc. Chem. Res. 2003, 36, 66-77 10.1021/ar020094c |
|
4-nitrobenzodifuroxan (NBDF)  |
E Param.: -6.15 |
|
Chem. Eur. J. 2007, 13, 8317-8324 10.1002/chem.200700676 |
|
(S,E)-5-benzyl-2,2,3-trimethyl-1-((E)-3-(3-nitrophenyl)allylidene)-4-oxoimidazolidin-1-ium  |
dichloromethane | E Param.: -6.10 |
|
Asian J. Org. Chem. 2014, 3, 550-555 10.1002/ajoc.201402009 |
(S,E)-2,2,3-trimethyl-4-oxo-5-((perfluorophenyl)methyl)-1-((E)-3-phenylallylidene)imidazolidin-1-ium  |
dichloromethane | E Param.: -6.00 |
|
Angew. Chem. Int. Ed. 2013, 52, 7967-7971 10.1002/anie.201301864 |
(S,E)-5-benzyl-1-((E)-3-(4-cyanophenyl)allylidene)-2,2,3-trimethyl-4-oxoimidazolidin-1-ium  |
dichloromethane | E Param.: -6.00 |
|
Asian J. Org. Chem. 2014, 3, 550-555 10.1002/ajoc.201402009 |
bis(1-methylindol-3-yl)methylium ion  |
E Param.: -5.99 |
|
J. Org. Chem. 2015, 80, 8643-8656 10.1021/acs.joc.5b01298 |
|
2-phenyl-1,3-dithiolan-2-ylium ion  |
E Param.: -5.91, Deviation: ±0.33 |
|
Acc. Chem. Res. 2003, 36, 66-77 10.1021/ar020094c |
|
(S,E)-5-benzyl-2,2,3-trimethyl-1-((E)-3-(4-nitrophenyl)allylidene)-4-oxoimidazolidin-1-ium  |
dichloromethane | E Param.: -5.90 |
|
Asian J. Org. Chem. 2014, 3, 550-555 10.1002/ajoc.201402009 |
(2S,5S)-5-benzyl-3-methyl-4-oxo-1-(3-phenylallylidene)-2-((E)-styryl)imidazolidin-1-ium  |
dichloromethane | E Param.: -5.90 |
|
Asian J. Org. Chem. 2014, 3, 550-555 10.1002/ajoc.201402009 |
(mpa)2CH+  |
E Param.: -5.89 |
|
J. Am. Chem. Soc. 2001, 123, 9500-9512 10.1021/ja010890y |
|
4-aza-6-nitrobenzofuroxan  |
E Param.: -5.86, Deviation: ±0.36 |
|
J. Org. Chem. 2005, 70, 6242-6253 10.1021/jo0505526 |
|
Vilsmeier ion  |
E Param.: -5.77 |
|
Acc. Chem. Res. 2003, 36, 66-77 10.1021/ar020094c |