C-Electrophiles
Name | Solvent |
Reactivity Parameters |
Classification |
Reference (title or year) |
---|---|---|---|---|
ethenylsulfonylbenzene (in DMSO)![]() ![]() |
DMSO | E Param.: -18.36 | ![]() ![]() ![]() | J. Am. Chem. Soc. 2017, 139, 13318-13329 10.1021/jacs.7b05106 |
acrylonitrile (in DMSO)![]() ![]() |
DMSO | E Param.: -19.05 | ![]() ![]() ![]() | J. Am. Chem. Soc. 2017, 139, 13318-13329 10.1021/jacs.7b05106 |
but-3-en-2-one (in DMSO)![]() ![]() |
DMSO | E Param.: -16.76 | ![]() ![]() ![]() | J. Am. Chem. Soc. 2017, 139, 13318-13329 10.1021/jacs.7b05106 |
1-phenylprop-2-en-1-one (in DMSO)![]() ![]() |
DMSO | E Param.: -15.25 | ![]() ![]() ![]() | J. Am. Chem. Soc. 2017, 139, 13318-13329 10.1021/jacs.7b05106 |
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[...] |
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-mesityl-3-methyl-1H-imidazol-3-ium![]() ![]() |
DMSO | E Param.: -11.48 | ![]() ![]() ![]() | 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-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[...] |
2-methylcyclopentenone![]() ![]() |
DMSO | E Param.: -22.10 | ![]() ![]() ![]() | Chem. Sci. 2021, 12, 4850-4865 10.1039/D0SC06628A |
cyclopentenone![]() ![]() |
DMSO | E Param.: -20.60 | ![]() ![]() ![]() | Chem. Sci. 2021, 12, 4850-4865 10.1039/D0SC06628A |
furan-2(5H)-one![]() ![]() |
DMSO | E Param.: -20.70 | ![]() ![]() ![]() | Chem. Sci. 2021, 12, 4850-4865 10.1039/D0SC06628A |
cyclohexenone![]() ![]() |
DMSO | E Param.: -22.10 | ![]() ![]() ![]() | Chem. Sci. 2021, 12, 4850-4865 10.1039/D0SC06628A |
3-methylenetetrahydropyran-2-one![]() ![]() |
DMSO | E Param.: -19.50 | ![]() ![]() ![]() | Chem. Sci. 2021, 12, 4850-4865 10.1039/D0SC06628A |
3-methylenedihydrofuranone![]() ![]() |
DMSO | E Param.: -19.40 | ![]() ![]() ![]() | Chem. Sci. 2021, 12, 4850-4865 10.1039/D0SC06628A |
(E)-2,6-di-tert-butyl-4-(3-phenylallylidene)cyclohexa-2,5-dien-1-one![]() ![]() |
DMSO | E Param.: -17.00 | ![]() ![]() ![]() | Org. Lett. 2020, 22, 2182-2186 10.1021/acs.orglett.[...] |
E)-2,6-di-tert-butyl-4-(3-(4-chlorophenyl)allylidene)cyclohexa-2,5-dien-1-one![]() ![]() |
DMSO | E Param.: -16.84 | ![]() ![]() ![]() | Org. Lett. 2020, 22, 2182-2186 10.1021/acs.orglett.[...] |
(E)-2,6-di-tert-butyl-4-(3-(4-nitrophenyl)allylidene)cyclohexa-2,5-dien-1-one![]() ![]() |
DMSO | E Param.: -16.25 | ![]() ![]() ![]() | Org. Lett. 2020, 22, 2182-2186 10.1021/acs.orglett.[...] |
(E)-2,6-di-tert-butyl-4-(3-(4-methoxyphenyl)allylidene)cyclohexa-2,5-dien-1-one![]() ![]() |
DMSO | E Param.: -17.42 | ![]() ![]() ![]() | Org. Lett. 2020, 22, 2182-2186 10.1021/acs.orglett.[...] |
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 |
3-nitro-1-tosyl-1H-indole![]() ![]() |
E Param.: -14.87 | ![]() ![]() ![]() | Chem. Commun. 2021, 57, 10071-10074 10.1039/d1cc04074j | |
phenyl isocyanate![]() ![]() |
MeCN | E Param.: -15.38 | ![]() ![]() ![]() | J. Am. Chem. Soc. 2020, 142, 8383-8402 10.1021/jacs.0c01960 |
p-tosyl isocyanate![]() ![]() |
MeCN | E Param.: -7.69 | ![]() ![]() ![]() | J. Am. Chem. Soc. 2020, 142, 8383-8402 10.1021/jacs.0c01960 |
phenyl isothiocyanate![]() ![]() |
DMSO | E Param.: -18.15 | ![]() ![]() ![]() | J. Am. Chem. Soc. 2020, 142, 8383-8402 10.1021/jacs.0c01960 |
p-nitrophenyl isothiocyanate![]() ![]() |
DMSO | E Param.: -15.89 | ![]() ![]() ![]() | J. Am. Chem. Soc. 2020, 142, 8383-8402 10.1021/jacs.0c01960 |
diphenylcarbodiimide![]() ![]() |
DMSO | E Param.: -20.14 | ![]() ![]() ![]() | J. Am. Chem. Soc. 2020, 142, 8383-8402 10.1021/jacs.0c01960 |
carbon disulfide![]() ![]() |
DMSO | E Param.: -17.70 | ![]() ![]() ![]() | J. Am. Chem. Soc. 2020, 142, 8383-8402 10.1021/jacs.0c01960 |
3,6-dinitro-1-tosyl-1H-indole![]() ![]() |
E Param.: -12.90 | ![]() ![]() ![]() | Chem. Commun. 2021, 57, 10071-10074 10.1039/d1cc04074j | |
cycloheptenone![]() ![]() |
DMSO | E Param.: -22.00 | ![]() ![]() ![]() | Chem. Sci. 2021, 12, 4850-4865 10.1039/D0SC06628A |
Umemoto I (triflate)![]() ![]() |
E Param.: -13.08 | ![]() ![]() ![]() | Eur. J. Org. Chem. 2024, 27, e202400085 10.1002/ejoc.202400085 | |
Umemoto I (tetrafluoroborate)![]() ![]() |
E Param.: -13.39 | ![]() ![]() ![]() | Eur. J. Org. Chem. 2024, 27, e202400085 10.1002/ejoc.202400085 | |
Umemoto II (triflate)![]() ![]() |
E Param.: -12.80 | ![]() ![]() ![]() | Eur. J. Org. Chem. 2024, 27, e202400085 10.1002/ejoc.202400085 | |
bh6a![]() ![]() |
E Param.: -18.60 | ![]() ![]() | Chem. Eur. J. 2010, 16, 1365-1371 10.1002/chem.200902487 | |
bh 6f![]() ![]() |
E Param.: -18.90 | ![]() ![]() | Chem. Eur. J. 2010, 16, 1365-1371 10.1002/chem.200902487 | |
bh 6i![]() ![]() |
E Param.: -19.10 | ![]() ![]() | Chem. Eur. J. 2010, 16, 1365-1371 10.1002/chem.200902487 | |
bh6j![]() ![]() |
E Param.: -17.90 | ![]() ![]() | Chem. Eur. J. 2010, 16, 1365-1371 10.1002/chem.200902487 | |
diarylallylium ion (3-F)2![]() ![]() |
E Param.: 4.15 | ![]() ![]() | J. Org. Chem. 2011, 76, 9391-9408 10.1021/jo201668w | |
indolecarboxylate derived iminium ion![]() ![]() |
dichloromethane | E Param.: -9.50 | ![]() ![]() | Angew. Chem. Int. Ed. 2009, 48, 5034-5037 10.1002/anie.200900933 |
(tfm)2CH+![]() ![]() |
E Param.: 7.96 | ![]() ![]() | J. Am. Chem. Soc. 2012, 134, 13902-13911 10.1021/ja306522b | |
(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)-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 |
(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 |
(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 |
(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 |
(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 |
(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 |
(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)-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 |
(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 |
p-quinone (C-H)![]() ![]() |
E Param.: -16.19 | ![]() ![]() | J. Am. Chem. Soc. 2014, 136, 11499-11512 10.1021/ja505613b | |
(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 | |
ethyl 2-methylprop-2-enoate (in DMSO)![]() ![]() |
DMSO | E Param.: -22.77 | ![]() ![]() | J. Am. Chem. Soc. 2017, 139, 13318-13329 10.1021/jacs.7b05106 |
ethyl (E)-but-2-enoate (in DMSO)![]() ![]() |
DMSO | E Param.: -23.59 | ![]() ![]() | J. Am. Chem. Soc. 2017, 139, 13318-13329 10.1021/jacs.7b05106 |
ethyl cinnamate (in DMSO)![]() ![]() |
DMSO | E Param.: -24.52 | ![]() ![]() | J. Am. Chem. Soc. 2017, 139, 13318-13329 10.1021/jacs.7b05106 |
(E)-1-methyl-4-(styrylsulfonyl)benzene (in DMSO)![]() ![]() |
DMSO | E Param.: -24.69 | ![]() ![]() | J. Am. Chem. Soc. 2017, 139, 13318-13329 10.1021/jacs.7b05106 |
dihydro-2H-pyran-2-one![]() ![]() |
DMSO | E Param.: -21.80 | ![]() ![]() | Chem. Sci. 2021, 12, 4850-4865 10.1039/D0SC06628A |
ethyl 3-nitro-1H-indole-1-carboxylate![]() ![]() |
E Param.: -14.10 | ![]() ![]() | Chem. Commun. 2021, 57, 10071-10074 10.1039/d1cc04074j | |
4-bromo-3-nitro-1-tosyl-1H-indole![]() ![]() |
E Param.: -14.60 | ![]() ![]() | Chem. Commun. 2021, 57, 10071-10074 10.1039/d1cc04074j | |
fc(Me)CH+![]() ![]() |
E Param.: -2.57 | ![]() | Acc. Chem. Res. 2003, 36, 66-77 10.1021/ar020094c | |
dimethylmethyleneammonium ion![]() ![]() |
E Param.: -6.69 | ![]() | Acc. Chem. Res. 2003, 36, 66-77 10.1021/ar020094c | |
methyl(phenyl)methyleneammonium ion![]() ![]() |
E Param.: -5.17 | ![]() | Acc. Chem. Res. 2003, 36, 66-77 10.1021/ar020094c | |
Vilsmeier ion![]() ![]() |
E Param.: -5.77 | ![]() | Acc. Chem. Res. 2003, 36, 66-77 10.1021/ar020094c | |
(2,4,6-trimethylphenyl)ethylium ion![]() ![]() |
E Param.: 6.04 | ![]() | Macromolecules 2005, 38, 33-40 10.1021/ma048389o | |
1,3-bis(2,4,6-trimethylphenyl)but-1-ylium ion![]() ![]() |
E Param.: 6.16 | ![]() | Macromolecules 2005, 38, 33-40 10.1021/ma048389o | |
diethyl 2-((1-methyl-1,2,3,4-tetrahydroquinolin-6-yl)methylene)malonate![]() ![]() |
E Param.: -23.40 | ![]() | Chem. Eur. J. 2008, 14, 9675-9682 10.1002/chem.200801277 | |
diethyl 2-((julolidine-9-yl)methylene)malonate![]() ![]() |
E Param.: -23.80 | ![]() | Chem. Eur. J. 2008, 14, 9675-9682 10.1002/chem.200801277 | |
pipN+=CH-CH-Ph![]() ![]() |
E Param.: -10.30 | ![]() | Angew. Chem. Int. Ed. 2008, 47, 8723-8726 10.1002/anie.200802889 | |
bh 6k![]() ![]() |
E Param.: -18.20 | ![]() | Chem. Eur. J. 2010, 16, 1365-1371 10.1002/chem.200902487 | |
bh 6l![]() ![]() |
E Param.: -18.90 | ![]() | Chem. Eur. J. 2010, 16, 1365-1371 10.1002/chem.200902487 | |
bh 6m![]() ![]() |
E Param.: -17.30 | ![]() | Chem. Eur. J. 2010, 16, 1365-1371 10.1002/chem.200902487 | |
1,2-diaza-1,3-diene 1e![]() ![]() |
MeOH | E Param.: -14.90 | ![]() | Chem. Eur. J. 2010, 16, 12008-12016 10.1002/chem.201000828 |
1,2-diaza-1,3-diene 1f![]() ![]() |
MeOH | E Param.: -15.30 | ![]() | Chem. Eur. J. 2010, 16, 12008-12016 10.1002/chem.201000828 |
(E)-4-(4-nitrophenyl)but-3-en-2-one (in DSMO)![]() ![]() |
DMSO | E Param.: -19.36 | ![]() | J. Am. Chem. Soc. 2011, 133, 8240-8251 10.1021/ja200820m |
(E)-4-methyl-1-(4-nitrophenyl)pent-1-en-3-one (in DMSO)![]() ![]() |
DMSO | E Param.: -19.17 | ![]() | J. Am. Chem. Soc. 2011, 133, 8240-8251 10.1021/ja200820m |
(E)-4,4-dimethyl-1-(4-nitrophenyl)pent-1-en-3-one![]() ![]() |
DMSO | E Param.: -19.15 | ![]() | J. Am. Chem. Soc. 2011, 133, 8240-8251 10.1021/ja200820m |
benzaldehyde (in DMSO)![]() ![]() |
DMSO | E Param.: -12.90 | ![]() | J. Am. Chem. Soc. 2018, 140, 5500-5515 10.1021/jacs.8b01657 |
(4-F)-tritylium ion![]() ![]() |
E Param.: 0.35 | ![]() | Eur. J. Org. Chem. 2011, , 6470-6475 10.1002/ejoc.201100910 | |
(4-F)2-tritylium ion![]() ![]() |
E Param.: 0.17 | ![]() | Eur. J. Org. Chem. 2011, , 6470-6475 10.1002/ejoc.201100910 | |
(4-F)3-tritylium ion![]() ![]() |
E Param.: 0.05 | ![]() | Eur. J. Org. Chem. 2011, , 6470-6475 10.1002/ejoc.201100910 | |
(3-F)-tritylium ion![]() ![]() |
E Param.: 1.01 | ![]() | Eur. J. Org. Chem. 2011, , 6470-6475 10.1002/ejoc.201100910 | |
(3-F)2-tritylium ion![]() ![]() |
E Param.: 1.54 | ![]() | Eur. J. Org. Chem. 2011, , 6470-6475 10.1002/ejoc.201100910 | |
(3-F)3-tritylium ion![]() ![]() |
E Param.: 2.07 | ![]() | Eur. J. Org. Chem. 2011, , 6470-6475 10.1002/ejoc.201100910 | |
(3-F)4-tritylium ion![]() ![]() |
E Param.: 2.54 | ![]() | Eur. J. Org. Chem. 2011, , 6470-6475 10.1002/ejoc.201100910 | |
diarylallylium ion (4-Cl)2![]() ![]() |
E Param.: 2.69 | ![]() | J. Org. Chem. 2011, 76, 9391-9408 10.1021/jo201668w | |
(dfp)2CH+![]() ![]() |
E Param.: 8.02 | ![]() | J. Am. Chem. Soc. 2012, 134, 13902-13911 10.1021/ja306522b | |
(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 |
cinnamonitrile (in DMSO)![]() ![]() |
DMSO | E Param.: -24.60 | ![]() | J. Am. Chem. Soc. 2017, 139, 13318-13329 10.1021/jacs.7b05106 |
cyclobutanone (in DMSO)![]() ![]() |
DMSO | E Param.: -17.50 | ![]() | J. Am. Chem. Soc. 2018, 140, 5500-5515 10.1021/jacs.8b01657 |
cyclopentanone (in DMSO)![]() ![]() |
DMSO | E Param.: -21.00 | ![]() | J. Am. Chem. Soc. 2018, 140, 5500-5515 10.1021/jacs.8b01657 |
cyclohexanone (in DMSO)![]() ![]() |
DMSO | E Param.: -19.90 | ![]() | J. Am. Chem. Soc. 2018, 140, 5500-5515 10.1021/jacs.8b01657 |
cycloheptanone (in DMSO)![]() ![]() |
DMSO | E Param.: -22.10 | ![]() | J. Am. Chem. Soc. 2018, 140, 5500-5515 10.1021/jacs.8b01657 |
1-methylpiperidin-4-one (in DMSO)![]() ![]() |
DMSO | E Param.: -18.40 | ![]() | J. Am. Chem. Soc. 2018, 140, 5500-5515 10.1021/jacs.8b01657 |
oxan-4-one (in DMSO)![]() ![]() |
DMSO | E Param.: -17.90 | ![]() | J. Am. Chem. Soc. 2018, 140, 5500-5515 10.1021/jacs.8b01657 |
thian-4-one (in DMSO)![]() ![]() |
DMSO | E Param.: -16.90 | ![]() | J. Am. Chem. Soc. 2018, 140, 5500-5515 10.1021/jacs.8b01657 |
1,4-dioxaspiro[4.5]decan-8-one (in DMSO)![]() ![]() |
DMSO | E Param.: -18.20 | ![]() | J. Am. Chem. Soc. 2018, 140, 5500-5515 10.1021/jacs.8b01657 |
pentan-2-one (in DMSO)![]() ![]() |
DMSO | E Param.: -22.30 | ![]() | J. Am. Chem. Soc. 2018, 140, 5500-5515 10.1021/jacs.8b01657 |
1-methylsulfanylpropan-2-one (in DMSO)![]() ![]() |
DMSO | E Param.: -15.60 | ![]() | J. Am. Chem. Soc. 2018, 140, 5500-5515 10.1021/jacs.8b01657 |
3-methylcyclopentenone![]() ![]() |
DMSO | E Param.: -28.90 | ![]() | Chem. Sci. 2021, 12, 4850-4865 10.1039/D0SC06628A |
2-methylcyclohexenone![]() ![]() |
DMSO | E Param.: -27.50 | ![]() | Chem. Sci. 2021, 12, 4850-4865 10.1039/D0SC06628A |
3-methylcyclohexenone![]() ![]() |
DMSO | E Param.: -29.60 | ![]() | Chem. Sci. 2021, 12, 4850-4865 10.1039/D0SC06628A |