Electrophiles
| Name | Solvent |
Reactivity Parameters |
Classification |
Reference (title or year) |
|---|---|---|---|---|
(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 |
|
2,3,4,5,6,6-hexachlorocyclohexa-2,4-dien-1-one  |
MeCN | E Param.: -6.75 |
|
Org. Lett. 2010, 12, 2238-2241 10.1021/ol100592j |
dimethylmethyleneammonium ion  |
E Param.: -6.69 |
|
Acc. Chem. Res. 2003, 36, 66-77 10.1021/ar020094c |
|
N-(trifluoromethyl)thio)saccharin  |
E Param.: -6.48 |
|
Angew. Chem. Int. Ed. 2018, 57, 12690-12695 10.1002/anie.201805859 |
|
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 |
N-(phenylsulfonyl)-N-((trifluoromethyl)thio)benzenesulfonamide  |
E Param.: -6.06 |
|
Angew. Chem. Int. Ed. 2018, 57, 12690-12695 10.1002/anie.201805859 |
|
(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 |
|
(mor)2CH+  |
E Param.: -5.53 |
|
J. Am. Chem. Soc. 2001, 123, 9500-9512 10.1021/ja010890y |
|
MacMillan-iminium ion (2nd generation)  |
MeCN | E Param.: -5.52 |
|
Angew. Chem. Int. Ed. 2011, 50, 9953-9956 10.1002/anie.201103683 |
4,6-dinitrobenzofurazan  |
E Param.: -5.46, Deviation: ±0.36 |
|
J. Org. Chem. 2005, 70, 6242-6253 10.1021/jo0505526 |
|
N-fluoro-2,6-dichloropyridinium tetrafluoroborate  |
E Param.: -5.29 |
|
J. Am. Chem. Soc. 2018, 140, 11474-11486 10.1021/jacs.8b07147 |
|
Selectfluor  |
E Param.: -5.20 |
|
J. Am. Chem. Soc. 2018, 140, 11474-11486 10.1021/jacs.8b07147 |
|
methyl(phenyl)methyleneammonium ion  |
E Param.: -5.17 |
|
Acc. Chem. Res. 2003, 36, 66-77 10.1021/ar020094c |
|
(E)-2-methyl-3-(4-methylbenzylidene)-3H-indol-1-ium ion  |
E Param.: -5.15 |
|
J. Org. Chem. 2015, 80, 8643-8656 10.1021/acs.joc.5b01298 |
|
4,6-dinitrobenzofuroxan  |
E Param.: -5.06 |
|
J. Org. Chem. 2006, 71, 9088-9095 10.1021/jo0614339 |
|
(E)-2-(tert-butyl)-3-(4-methylbenzylidene)-3H-indol-1-ium  |
dichloromethane | E Param.: -5.06 |
|
Eur. J. Org. Chem. 2016, , 4050-4058 10.1002/ejoc.201600572 |
(E)-1,2-dimethyl-3-(4-methylbenzylidene)-3H-indol-1-ium ion  |
E Param.: -5.05 |
|
J. Org. Chem. 2015, 80, 8643-8656 10.1021/acs.joc.5b01298 |
|
(E)-3-benzylidene-1,2-dimethyl-3H-indol-1-ium ion  |
E Param.: -4.96 |
|
J. Org. Chem. 2015, 80, 8643-8656 10.1021/acs.joc.5b01298 |
|
2-(4-methoxyphenyl)chromenylium ion  |
E Param.: -4.95, Deviation: ±0.06 |
|
Acc. Chem. Res. 2003, 36, 66-77 10.1021/ar020094c |
|
4-nitro-6-(trifluoromethylsulfonyl)benzofuroxan  |
E Param.: -4.91, Deviation: ±0.31 |
|
J. Org. Chem. 2005, 70, 6242-6253 10.1021/jo0505526 |
|
(dpa)2CH+  |
E Param.: -4.72 |
|
J. Am. Chem. Soc. 2001, 123, 9500-9512 10.1021/ja010890y |
|
4,6-dinitrotetrazolopyridine  |
E Param.: -4.67, Deviation: ±0.30 |
|
J. Org. Chem. 2005, 70, 6242-6253 10.1021/jo0505526 |
|
9-(4-(dimethylamino)phenyl)-9H-fluoren-9-ylium  |
dichloromethane | E Param.: -4.51 |
|
Chem. Eur. J. 2017, 23, 623-630 10.1002/chem.201603963 |
(4-MeO)3-tritylium ion  |
E Param.: -4.35 |
 |
J. Am. Chem. Soc. 2003, 125, 286-295 10.1021/ja021010y |
|
(mfa)2CH+  |
E Param.: -3.85 |
|
J. Am. Chem. Soc. 2001, 123, 9500-9512 10.1021/ja010890y |
|
tropylium ion  |
E Param.: -3.72, Deviation: ±0.03 |
|
Acc. Chem. Res. 2003, 36, 66-77 10.1021/ar020094c |
|
2,3-dichloro-5,6-dicyano-p-benzoquinone (DDQ)  |
MeCN | E Param.: -3.66 |
|
J. Am. Chem. Soc. 2013, 135, 12377-12387 10.1021/ja405890d |
C7H7+-Fe(CO)3  |
E Param.: -3.49, Deviation: ±0.17 |
|
Acc. Chem. Res. 2003, 36, 66-77 10.1021/ar020094c |
|
flavylium ion  |
E Param.: -3.45, Deviation: ±0.16 |
|
Acc. Chem. Res. 2003, 36, 66-77 10.1021/ar020094c |
|
(pfa)2CH+  |
E Param.: -3.14 |
|
J. Am. Chem. Soc. 2001, 123, 9500-9512 10.1021/ja010890y |
|
(4-MeO)2-tritylium ion  |
E Param.: -3.04 |
|
J. Am. Chem. Soc. 2003, 125, 286-295 10.1021/ja021010y |
|
3-(4-methoxybenzylidene)-1-methyl-3H-indol-1-ium iom  |
E Param.: -3.02 |
|
J. Org. Chem. 2015, 80, 8643-8656 10.1021/acs.joc.5b01298 |
|
fc(ani)CH+  |
E Param.: -2.90, Deviation: ±0.09 |
|
Acc. Chem. Res. 2003, 36, 66-77 10.1021/ar020094c |
|
Me2C=C=N(+)Me2  |
E Param.: -2.80 |
|
Synthesis 2025, 57, 3251-3262 10.1055/a-2649-1999 |