C-Electrophiles
| Name | Solvent |
Reactivity Parameters |
Classification |
Reference (title or year) |
|---|---|---|---|---|
tritylium ion (Ph3C+)   |
E Param.: 0.51 |
 |
J. Am. Chem. Soc. 2003, 125, 286-295 10.1021/ja021010y |
|
(4-CF3)2-tritylium ion  |
E Param.: 2.28 |
|
J. Am. Chem. Soc. 2003, 125, 286-295 10.1021/ja021010y |
|
(3-Cl)3-tritylium ion  |
E Param.: 1.99 |
|
J. Am. Chem. Soc. 2003, 125, 286-295 10.1021/ja021010y |
|
(4-CF3)-tritylium ion  |
E Param.: 1.33 |
|
J. Am. Chem. Soc. 2003, 125, 286-295 10.1021/ja021010y |
|
(3-Cl)-tritylium ion  |
E Param.: 1.06 |
|
J. Am. Chem. Soc. 2003, 125, 286-295 10.1021/ja021010y |
|
(3-CF3)-tritylium ion  |
E Param.: 1.18 |
|
J. Am. Chem. Soc. 2003, 125, 286-295 10.1021/ja021010y |
|
(4-Me)-tritylium ion  |
E Param.: -0.13 |
|
J. Am. Chem. Soc. 2003, 125, 286-295 10.1021/ja021010y |
|
(4-Me)2-tritylium ion  |
E Param.: -0.70 |
|
J. Am. Chem. Soc. 2003, 125, 286-295 10.1021/ja021010y |
|
(4-Me)3-tritylium ion  |
E Param.: -1.21 |
|
J. Am. Chem. Soc. 2003, 125, 286-295 10.1021/ja021010y |
|
(4-MeO,3-OMe)-tritylium ion  |
E Param.: -1.62 |
|
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 |
|
(4-MeO)-tritylium ion  |
E Param.: -1.59 |
|
Eur. J. Org. Chem. 2011, , 6470-6475 10.1002/ejoc.201100910 |
|
(4-MeO,4-Me)-tritylium ion  |
E Param.: -2.13 |
|
J. Am. Chem. Soc. 2003, 125, 286-295 10.1021/ja021010y |
|
(4-MeO)2-tritylium ion  |
E Param.: -3.04 |
|
J. Am. Chem. Soc. 2003, 125, 286-295 10.1021/ja021010y |
|
(4-MeO)3-tritylium ion  |
E Param.: -4.35 |
|
J. Am. Chem. Soc. 2003, 125, 286-295 10.1021/ja021010y |
|
(4-NMe2)-tritylium ion  |
E Param.: -7.93 |
|
J. Am. Chem. Soc. 2003, 125, 286-295 10.1021/ja021010y |
|
(4-NMe2)2-tritylium ion (= Malachite green)  |
E Param.: -10.29 |
|
J. Am. Chem. Soc. 2003, 125, 286-295 10.1021/ja021010y |
|
(4-NMe2)3-tritylium ion (= Crystal violet)  |
E Param.: -11.26 |
|
J. Am. Chem. Soc. 2003, 125, 286-295 10.1021/ja021010y |
|
3-chloro-benzaldehyde (in DMSO)  |
DMSO | |
J. Am. Chem. Soc. 2011, 133, 8240-8251 10.1021/ja200820m |
|
3-fluoro-benzaldehyde (in DMSO)  |
DMSO | |
J. Am. Chem. Soc. 2011, 133, 8240-8251 10.1021/ja200820m |
|
3-methoxy-benzaldehyde (in DMSO)  |
DMSO | |
J. Am. Chem. Soc. 2011, 133, 8240-8251 10.1021/ja200820m |
|
4-fluoro-benzaldehyde (in DMSO)  |
DMSO | |
J. Am. Chem. Soc. 2011, 133, 8240-8251 10.1021/ja200820m |
|
hexanal (in DMSO)  |
DMSO | |
J. Am. Chem. Soc. 2011, 133, 8240-8251 10.1021/ja200820m |
|
butanal (in DMSO)  |
DMSO | |
J. Am. Chem. Soc. 2011, 133, 8240-8251 10.1021/ja200820m |
|
cinnamaldehyde (in DMSO)  |
DMSO | |
J. Am. Chem. Soc. 2011, 133, 8240-8251 10.1021/ja200820m |
|
p-nitro-cinnamaldehyde (in DMSO)  |
DMSO | |
J. Am. Chem. Soc. 2011, 133, 8240-8251 10.1021/ja200820m |
|
dibenzo[a,d]tropylium ion  |
dichloromethane | E Param.: -0.63 |
|
Liebigs Ann. 1995, , 2005-2009 10.1002/jlac.1995199[...] |
4-phenylbut-3-yn-2-one  |
E Param.: -16.90 |
|
Angew. Chem. Int. Ed. 2019, 58, 17704-17708 10.1002/anie.201909803 |
|
hex-3-yn-2-one  |
E Param.: -17.90 |
|
Angew. Chem. Int. Ed. 2019, 58, 17704-17708 10.1002/anie.201909803 |
|
butynone  |
E Param.: -16.60 |
|
Angew. Chem. Int. Ed. 2019, 58, 17704-17708 10.1002/anie.201909803 |
|
Me2C=C=N(+)Me2  |
E Param.: -2.80 |
|
Synthesis 2025, 57, 3251-3262 10.1055/a-2649-1999 |
|
Ph2C=C=N(+)Me2  |
E Param.: -1.90 |
|
Synthesis 2025, 57, 3251-3262 10.1055/a-2649-1999 |
|
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 |
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 |