Electrophiles
| Name | Solvent |
Reactivity Parameters |
Classification |
Reference (title or year) |
|---|---|---|---|---|
(dfp)2CH+   |
E Param.: 8.02 |
 |
J. Am. Chem. Soc. 2012, 134, 13902-13911 10.1021/ja306522b |
|
(tfm)2CH+  |
E Param.: 7.96 |
|
J. Am. Chem. Soc. 2012, 134, 13902-13911 10.1021/ja306522b |
|
(dfp)(mfp)CH+  |
E Param.: 7.52 |
|
J. Am. Chem. Soc. 2012, 134, 13902-13911 10.1021/ja306522b |
|
(mfp)2CH+  |
E Param.: 6.87 |
|
J. Am. Chem. Soc. 2012, 134, 13902-13911 10.1021/ja306522b |
|
(dfp)PhCH+  |
E Param.: 6.74 |
|
J. Am. Chem. Soc. 2012, 134, 13902-13911 10.1021/ja306522b |
|
(tfm)PhCH+  |
E Param.: 6.70 |
|
J. Am. Chem. Soc. 2012, 134, 13902-13911 10.1021/ja306522b |
|
(mfp)PhCH+  |
E Param.: 6.23 |
|
J. Am. Chem. Soc. 2012, 134, 13902-13911 10.1021/ja306522b |
|
1,3-bis(2,4,6-trimethylphenyl)but-1-ylium ion  |
E Param.: 6.16 |
|
Macromolecules 2005, 38, 33-40 10.1021/ma048389o |
|
diarylallylium ion (3,3-F2)2  |
E Param.: 6.11 |
|
J. Org. Chem. 2011, 76, 9391-9408 10.1021/jo201668w |
|
(2,4,6-trimethylphenyl)ethylium ion  |
E Param.: 6.04 |
|
Macromolecules 2005, 38, 33-40 10.1021/ma048389o |
|
cumyl cation  |
E Param.: 5.74 |
|
Macromolecules 2010, 43, 1719-1723 10.1021/ma9024569 |
|
(pcp)2CH+  |
E Param.: 5.48 |
|
J. Am. Chem. Soc. 2012, 134, 13902-13911 10.1021/ja306522b |
|
benzhydrylium ion Ph2CH+  |
E Param.: 5.47 |
|
J. Am. Chem. Soc. 2012, 134, 13902-13911 10.1021/ja306522b |
|
(Ftol)2CH+  |
E Param.: 5.24 |
|
J. Am. Chem. Soc. 2012, 134, 13902-13911 10.1021/ja306522b |
|
pfp(Ph)CH+  |
E Param.: 5.20 |
|
J. Am. Chem. Soc. 2012, 134, 13902-13911 10.1021/ja306522b |
|
(pfp)2CH+  |
E Param.: 5.01, Deviation: ±0.05 |
|
J. Am. Chem. Soc. 2012, 134, 13902-13911 10.1021/ja306522b |
|
tol(Ph)CH+  |
E Param.: 4.43 |
|
J. Am. Chem. Soc. 2012, 134, 13902-13911 10.1021/ja306522b |
|
diarylallylium ion (3-F)2  |
E Param.: 4.15 |
|
J. Org. Chem. 2011, 76, 9391-9408 10.1021/jo201668w |
|
(tol)2CH+  |
E Param.: 3.63 |
|
J. Am. Chem. Soc. 2001, 123, 9500-9512 10.1021/ja010890y |
|
1-(4-chlorophenyl)cyclopent-2-enylium ion  |
E Param.: 3.20, Deviation: ±0.37 |
|
Acc. Chem. Res. 2003, 36, 66-77 10.1021/ar020094c |
|
methoxy-phenylmethylium ion  |
E Param.: 2.97, Deviation: ±0.09 |
|
Acc. Chem. Res. 2003, 36, 66-77 10.1021/ar020094c |
|
pop(Ph)CH+  |
E Param.: 2.90 |
|
J. Am. Chem. Soc. 2001, 123, 9500-9512 10.1021/ja010890y |
|
1-phenylcyclopent-2-enylium ion  |
E Param.: 2.89, Deviation: ±0.25 |
|
Acc. Chem. Res. 2003, 36, 66-77 10.1021/ar020094c |
|
diarylallylium ion (4-Br)2  |
E Param.: 2.85 |
|
J. Org. Chem. 2011, 76, 9391-9408 10.1021/jo201668w |
|
diphenylallylium ion  |
E Param.: 2.70 |
|
J. Org. Chem. 2011, 76, 9391-9408 10.1021/jo201668w |
|
diarylallylium ion (4-Cl)2  |
E Param.: 2.69 |
|
J. Org. Chem. 2011, 76, 9391-9408 10.1021/jo201668w |
|
(3-F)4-tritylium ion  |
E Param.: 2.54 |
|
Eur. J. Org. Chem. 2011, , 6470-6475 10.1002/ejoc.201100910 |
|
N-ethylidenecarbazolium ion  |
E Param.: 2.41, Deviation: ±0.33 |
|
Acc. Chem. Res. 2003, 36, 66-77 10.1021/ar020094c |
|
9-phenyl-9H-fluoren-9-ylium  |
dichloromethane | E Param.: 2.41 |
|
Chem. Eur. J. 2017, 23, 623-630 10.1002/chem.201603963 |
(4-CF3)2-tritylium ion  |
E Param.: 2.28 |
 |
J. Am. Chem. Soc. 2003, 125, 286-295 10.1021/ja021010y |
|
pop(tol)CH+  |
E Param.: 2.16, Deviation: ±0.03 |
|
Acc. Chem. Res. 2003, 36, 66-77 10.1021/ar020094c |
|
ani(Ph)CH+  |
E Param.: 2.11 |
|
J. Am. Chem. Soc. 2001, 123, 9500-9512 10.1021/ja010890y |
|
(3-F)3-tritylium ion  |
E Param.: 2.07 |
|
Eur. J. Org. Chem. 2011, , 6470-6475 10.1002/ejoc.201100910 |
|
(3-Cl)3-tritylium ion  |
E Param.: 1.99 |
|
J. Am. Chem. Soc. 2003, 125, 286-295 10.1021/ja021010y |
|
methoxy-(4-methylphenyl)methylium ion  |
E Param.: 1.90, Deviation: ±0.22 |
|
Acc. Chem. Res. 2003, 36, 66-77 10.1021/ar020094c |
|
(3-F)2-tritylium ion  |
E Param.: 1.54 |
|
Eur. J. Org. Chem. 2011, , 6470-6475 10.1002/ejoc.201100910 |
|
ani(tol)CH+  |
E Param.: 1.48 |
|
J. Am. Chem. Soc. 2001, 123, 9500-9512 10.1021/ja010890y |
|
4-chlorobenzaldehyde-boron trichloride complex  |
E Param.: 1.44, Deviation: ±0.20 |
|
Acc. Chem. Res. 2003, 36, 66-77 10.1021/ar020094c |
|
(4-CF3)-tritylium ion  |
E Param.: 1.33 |
|
J. Am. Chem. Soc. 2003, 125, 286-295 10.1021/ja021010y |
|
di-p-tolyl-allylium ion  |
E Param.: 1.23 |
|
J. Org. Chem. 2011, 76, 9391-9408 10.1021/jo201668w |
|
(3-CF3)-tritylium ion  |
E Param.: 1.18 |
|
J. Am. Chem. Soc. 2003, 125, 286-295 10.1021/ja021010y |
|
benzaldehyde-boron trichloride complex  |
E Param.: 1.12, Deviation: ±0.24 |
|
Acc. Chem. Res. 2003, 36, 66-77 10.1021/ar020094c |
|
1,3-diphenylpropyn-1-ylium-Cr(CO)3  |
E Param.: 1.07, Deviation: ±0.30 |
|
Acc. Chem. Res. 2003, 36, 66-77 10.1021/ar020094c |
|
(3-Cl)-tritylium ion  |
E Param.: 1.06 |
|
J. Am. Chem. Soc. 2003, 125, 286-295 10.1021/ja021010y |
|
(3-F)-tritylium ion  |
E Param.: 1.01 |
|
Eur. J. Org. Chem. 2011, , 6470-6475 10.1002/ejoc.201100910 |
|
1,1,3-triphenylallylium ion  |
E Param.: 0.98, Deviation: ±0.20 |
|
Acc. Chem. Res. 2003, 36, 66-77 10.1021/ar020094c |
|
9-(4-methoxyphenyl)-9H-fluoren-9-ylium  |
dichloromethane | E Param.: 0.85 |
|
Chem. Eur. J. 2017, 23, 623-630 10.1002/chem.201603963 |
ani(pop)CH+  |
E Param.: 0.61 |
|
J. Am. Chem. Soc. 2001, 123, 9500-9512 10.1021/ja010890y |
|
tritylium ion (Ph3C+)  |
E Param.: 0.51 |
|
J. Am. Chem. Soc. 2003, 125, 286-295 10.1021/ja021010y |
|
(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 |
|
methoxy-(4-methoxyphenyl)methylium ion  |
E Param.: 0.14, Deviation: ±0.01 |
|
Acc. Chem. Res. 2003, 36, 66-77 10.1021/ar020094c |
|
(4-F)3-tritylium ion  |
E Param.: 0.05 |
|
Eur. J. Org. Chem. 2011, , 6470-6475 10.1002/ejoc.201100910 |
|
(ani)2CH+  |
E Param.: 0.00 |
|
J. Am. Chem. Soc. 2001, 123, 9500-9512 10.1021/ja010890y |
|
(4-Me)-tritylium ion  |
E Param.: -0.13 |
|
J. Am. Chem. Soc. 2003, 125, 286-295 10.1021/ja021010y |
|
1,1,3-triphenylpropyn-1-ylium-Cr(CO)3  |
E Param.: -0.25, Deviation: ±0.20 |
|
Acc. Chem. Res. 2003, 36, 66-77 10.1021/ar020094c |
|
dibenzo[a,d]tropylium ion  |
dichloromethane | E Param.: -0.63 |
|
Liebigs Ann. 1995, , 2005-2009 10.1002/jlac.1995199[...] |
(4-Me)2-tritylium ion  |
E Param.: -0.70 |
|
J. Am. Chem. Soc. 2003, 125, 286-295 10.1021/ja021010y |
|
(fur)(ani)CH+  |
E Param.: -0.81 |
|
J. Am. Chem. Soc. 2012, 134, 13902-13911 10.1021/ja306522b |
|
propyn-1-ylium-Co2(CO)6  |
E Param.: -0.84, Deviation: ±0.36 |
|
Acc. Chem. Res. 2003, 36, 66-77 10.1021/ar020094c |
|
1-phenyl-proyn-ylium-Co2(CO)6  |
E Param.: -0.97, Deviation: ±0.08 |
|
Acc. Chem. Res. 2003, 36, 66-77 10.1021/ar020094c |
|
(4-Me)3-tritylium ion  |
E Param.: -1.21 |
|
J. Am. Chem. Soc. 2003, 125, 286-295 10.1021/ja021010y |
|
(fur)2CH+  |
E Param.: -1.36 |
|
J. Am. Chem. Soc. 2001, 123, 9500-9512 10.1021/ja010890y |
|
di-p-anisyl-allylium ion  |
E Param.: -1.45 |
|
J. Org. Chem. 2011, 76, 9391-9408 10.1021/jo201668w |
|
3-phenylpropyn-1-ylium-Co2(CO)6  |
E Param.: -1.58, Deviation: ±0.58 |
|
Acc. Chem. Res. 2003, 36, 66-77 10.1021/ar020094c |
|
(4-MeO)-tritylium ion  |
E Param.: -1.59 |
|
Eur. J. Org. Chem. 2011, , 6470-6475 10.1002/ejoc.201100910 |
|
3-(trimethylsilyl)propyn-1-ylium-Co2(CO)6  |
E Param.: -1.60, Deviation: ±0.34 |
|
Acc. Chem. Res. 2003, 36, 66-77 10.1021/ar020094c |
|
(4-MeO,3-OMe)-tritylium ion  |
E Param.: -1.62 |
|
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-OMe,3-Me)-tritylium ion  |
E Param.: -1.84 |
|
J. Am. Chem. Soc. 2003, 125, 286-295 10.1021/ja021010y |
|
Ph2C=C=N(+)Me2  |
E Param.: -1.90 |
|
Synthesis 2025, 57, 3251-3262 10.1055/a-2649-1999 |
|
(4-MeO,4-Me)-tritylium ion  |
E Param.: -2.13 |
|
J. Am. Chem. Soc. 2003, 125, 286-295 10.1021/ja021010y |
|
1,3-dithianylium ion  |
E Param.: -2.14, Deviation: ±0.07 |
|
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 |
|
fc(Me)CH+  |
E Param.: -2.57 |
|
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 |
|
1,1-dianisyl-3-phenylallylium ion  |
E Param.: -2.67, Deviation: ±0.30 |
|
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 |
|
fc(ani)CH+  |
E Param.: -2.90, Deviation: ±0.09 |
|
Acc. Chem. Res. 2003, 36, 66-77 10.1021/ar020094c |
|
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 |
|
(4-MeO)2-tritylium ion  |
E Param.: -3.04 |
|
J. Am. Chem. Soc. 2003, 125, 286-295 10.1021/ja021010y |
|
(pfa)2CH+  |
E Param.: -3.14 |
|
J. Am. Chem. Soc. 2001, 123, 9500-9512 10.1021/ja010890y |
|
flavylium ion  |
E Param.: -3.45, Deviation: ±0.16 |
|
Acc. Chem. Res. 2003, 36, 66-77 10.1021/ar020094c |
|
C7H7+-Fe(CO)3  |
E Param.: -3.49, Deviation: ±0.17 |
|
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 |
tropylium ion  |
E Param.: -3.72, Deviation: ±0.03 |
|
Acc. Chem. Res. 2003, 36, 66-77 10.1021/ar020094c |
|
(mfa)2CH+  |
E Param.: -3.85 |
|
J. Am. Chem. Soc. 2001, 123, 9500-9512 10.1021/ja010890y |
|
(4-MeO)3-tritylium ion  |
E Param.: -4.35 |
|
J. Am. Chem. Soc. 2003, 125, 286-295 10.1021/ja021010y |
|
9-(4-(dimethylamino)phenyl)-9H-fluoren-9-ylium  |
dichloromethane | E Param.: -4.51 |
|
Chem. Eur. J. 2017, 23, 623-630 10.1002/chem.201603963 |
4,6-dinitrotetrazolopyridine  |
E Param.: -4.67, Deviation: ±0.30 |
|
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-nitro-6-(trifluoromethylsulfonyl)benzofuroxan  |
E Param.: -4.91, Deviation: ±0.31 |
|
J. Org. Chem. 2005, 70, 6242-6253 10.1021/jo0505526 |
|
2-(4-methoxyphenyl)chromenylium ion  |
E Param.: -4.95, Deviation: ±0.06 |
|
Acc. Chem. Res. 2003, 36, 66-77 10.1021/ar020094c |
|
(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 |
|
(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 |
|
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)-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 |
|
methyl(phenyl)methyleneammonium ion  |
E Param.: -5.17 |
|
Acc. Chem. Res. 2003, 36, 66-77 10.1021/ar020094c |
|
Selectfluor  |
E Param.: -5.20 |
|
J. Am. Chem. Soc. 2018, 140, 11474-11486 10.1021/jacs.8b07147 |