Electrophiles
Name | Solvent |
Reactivity Parameters |
Classification |
Reference (title or year) |
---|---|---|---|---|
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 |
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 | ![]() ![]() ![]() | 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 | ![]() ![]() ![]() | J. Org. Chem. 2005, 70, 6242-6253 10.1021/jo0505526 | |
1,1-bis(4-dimethylaminophenyl)-3-phenylallylium ion![]() ![]() |
E Param.: -8.97 | ![]() ![]() ![]() | Acc. Chem. Res. 2003, 36, 66-77 10.1021/ar020094c | |
C6H6OMe+-Fe(CO)3![]() ![]() |
E Param.: -8.94 | ![]() ![]() ![]() | Acc. Chem. Res. 2003, 36, 66-77 10.1021/ar020094c | |
dibenzyl azodicarboxylate![]() ![]() |
MeCN | E Param.: -8.89 | ![]() ![]() ![]() | Chem. Eur. J. 2010, 16, 11670-11677 10.1002/chem.201001598 |
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 | ![]() ![]() ![]() | 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 | |
NFSI![]() ![]() |
MeCN | E Param.: -8.44 | ![]() ![]() ![]() | J. Am. Chem. Soc. 2018, 140, 11474-11486 10.1021/jacs.8b07147 |
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 | ![]() ![]() ![]() | 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 | ![]() ![]() ![]() | 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 | ![]() ![]() ![]() | 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 | ![]() ![]() ![]() | Acc. Chem. Res. 2003, 36, 66-77 10.1021/ar020094c | |
4-cyano-6-nitro-benzofuroxane![]() ![]() |
E Param.: -6.41 | ![]() ![]() ![]() | 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 | ![]() ![]() ![]() | 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 | ![]() ![]() ![]() | 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 | ![]() ![]() ![]() | 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 | ![]() ![]() ![]() | 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 | ![]() ![]() ![]() | Acc. Chem. Res. 2003, 36, 66-77 10.1021/ar020094c | |
4-nitro-6-(trifluoromethylsulfonyl)benzofuroxan![]() ![]() |
E Param.: -4.91 | ![]() ![]() ![]() | 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 | ![]() ![]() ![]() | 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 | ![]() ![]() ![]() | 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 | ![]() ![]() ![]() | Acc. Chem. Res. 2003, 36, 66-77 10.1021/ar020094c | |
flavylium ion![]() ![]() |
E Param.: -3.45 | ![]() ![]() ![]() | 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 | ![]() ![]() ![]() | Acc. Chem. Res. 2003, 36, 66-77 10.1021/ar020094c | |
1,1-dianisyl-3-phenylallylium ion![]() ![]() |
E Param.: -2.67 | ![]() ![]() ![]() | Acc. Chem. Res. 2003, 36, 66-77 10.1021/ar020094c | |
fc(Ph)CH+![]() ![]() |
E Param.: -2.64 | ![]() ![]() ![]() ![]() ![]() | J. Am. Chem. Soc. 2001, 123, 9500-9512 10.1021/ja010890y | |
fc(Me)CH+![]() ![]() |
E Param.: -2.57 | ![]() | Acc. Chem. Res. 2003, 36, 66-77 10.1021/ar020094c | |
1-methyl-3-(4-methylbenzylidene)-3H-indol-1-ium ion![]() ![]() |
E Param.: -2.19 | ![]() ![]() ![]() | J. Org. Chem. 2015, 80, 8643-8656 10.1021/acs.joc.5b01298 | |
1,3-dithianylium ion![]() ![]() |
E Param.: -2.14 | ![]() ![]() ![]() | Acc. Chem. Res. 2003, 36, 66-77 10.1021/ar020094c | |
(4-MeO,4-Me)-tritylium ion![]() ![]() |
E Param.: -2.13 | ![]() | J. Am. Chem. Soc. 2003, 125, 286-295 10.1021/ja021010y | |
(4-OMe,3-Me)-tritylium ion![]() ![]() |
E Param.: -1.84 | ![]() | J. Am. Chem. Soc. 2003, 125, 286-295 10.1021/ja021010y | |
3-benzylidene-1-methyl-3H-indol-1-ium ion![]() ![]() |
E Param.: -1.80 | ![]() ![]() ![]() | J. Org. Chem. 2015, 80, 8643-8656 10.1021/acs.joc.5b01298 | |
(4-MeO,3-OMe)-tritylium ion![]() ![]() |
E Param.: -1.62 | ![]() | J. Am. Chem. Soc. 2003, 125, 286-295 10.1021/ja021010y |