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 | |
diphenyldiazomethane![]() ![]() |
E Param.: -21.40 | ![]() | Chem. Eur. J. 2022, 28, e202201376 10.1002/chem.202201376 | |
butynone![]() ![]() |
E Param.: -16.60 | ![]() | Angew. Chem. Int. Ed. 2019, 58, 17704-17708 10.1002/anie.201909803 | |
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 |
N-methyl-N-((trifluoromethyl)thio)-aniline![]() ![]() |
E Param.: -23.32 | ![]() | Angew. Chem. Int. Ed. 2018, 57, 12690-12695 10.1002/anie.201805859 | |
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 |