Carbocations
| Name | Solvent |
Reactivity Parameters |
Classification |
Reference (title or year) |
|---|---|---|---|---|
(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 |
MacMillan-iminium ion (1st generation) |
MeCN | E Param.: -7.37 | | 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 | |
MacMillan-iminium ion (spiro) |
MeCN | E Param.: -7.67 | | Angew. Chem. Int. Ed. 2011, 50, 9953-9956 10.1002/anie.201103683 |
(pyr)2CH+ |
E Param.: -7.69 | | J. Am. Chem. Soc. 2001, 123, 9500-9512 10.1021/ja010890y | |
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 | |
(4-NMe2)-tritylium ion |
E Param.: -7.93 |  | J. Am. Chem. Soc. 2003, 125, 286-295 10.1021/ja021010y | |
(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 |
Jorgensen/Hayashi-iminium ion |
E Param.: -8.20 | | Angew. Chem. Int. Ed. 2008, 47, 8723-8726 10.1002/anie.200802889 | |
(thq)2CH+ |
E Param.: -8.22 | | J. Am. Chem. Soc. 2001, 123, 9500-9512 10.1021/ja010890y | |
p-CF3-C6H4-CH=N+Me2 (in MeCN) |
MeCN | E Param.: -8.34 | | J. Am. Chem. Soc. 2013, 135, 6579-6587 10.1021/ja401106x |
(PhCH2)2N+=CH-CH-Ph |
E Param.: -8.50 | | Angew. Chem. Int. Ed. 2008, 47, 8723-8726 10.1002/anie.200802889 | |
mor iminium |
E Param.: -8.60 | | Angew. Chem. Int. Ed. 2008, 47, 8723-8726 10.1002/anie.200802889 | |
(ind)2CH+ |
E Param.: -8.76 | | J. Am. Chem. Soc. 2001, 123, 9500-9512 10.1021/ja010890y | |
1,1-bis(4-dimethylaminophenyl)-3-phenylallylium ion |
E Param.: -8.97 | | 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 | |
PhCH=N+Me2 (in MeCN) |
MeCN | E Param.: -9.27 | | J. Am. Chem. Soc. 2013, 135, 6579-6587 10.1021/ja401106x |
PhCH=N+(CH2)4 (in MeCN) |
MeCN | E Param.: -9.35 | | J. Am. Chem. Soc. 2013, 135, 6579-6587 10.1021/ja401106x |
(jul)2CH+ |
E Param.: -9.45 | | J. Am. Chem. Soc. 2001, 123, 9500-9512 10.1021/ja010890y | |
indolecarboxylate derived iminium ion |
dichloromethane | E Param.: -9.50 | | Angew. Chem. Int. Ed. 2009, 48, 5034-5037 10.1002/anie.200900933 |
PhCH=N+(CH2)5 (in MeCN) |
MeCN | E Param.: -9.60 | | J. Am. Chem. Soc. 2013, 135, 6579-6587 10.1021/ja401106x |
pTolCH=N+CH2 (in MeCN) |
MeCN | E Param.: -9.64 | | J. Am. Chem. Soc. 2013, 135, 6579-6587 10.1021/ja401106x |
bis(julidin-9-yl)allylium ion |
E Param.: -9.78 | | J. Org. Chem. 2011, 76, 9391-9408 10.1021/jo201668w | |
pyrN+=CH-CH-Ph |
E Param.: -9.80 | | Angew. Chem. Int. Ed. 2008, 47, 8723-8726 10.1002/anie.200802889 | |
1,1,3-tris(4-(dimethylamino)phenyl)allylium ion |
E Param.: -9.84 | | Acc. Chem. Res. 2003, 36, 66-77 10.1021/ar020094c | |
(lil)2CH+ |
E Param.: -10.04 | | J. Am. Chem. Soc. 2001, 123, 9500-9512 10.1021/ja010890y | |
bis(1,2-dimethylindol-3-yl)methylium ion |
E Param.: -10.23 | | J. Org. Chem. 2015, 80, 8643-8656 10.1021/acs.joc.5b01298 | |
(4-NMe2)2-tritylium ion (= Malachite green) |
E Param.: -10.29 | | J. Am. Chem. Soc. 2003, 125, 286-295 10.1021/ja021010y | |
pipN+=CH-CH-Ph |
E Param.: -10.30 | | Angew. Chem. Int. Ed. 2008, 47, 8723-8726 10.1002/anie.200802889 | |
(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 |
p-AniCH=N+Me2 (in MeCN) |
MeCN | E Param.: -10.69 | | J. Am. Chem. Soc. 2013, 135, 6579-6587 10.1021/ja401106x |
(4-NMe2)3-tritylium ion (= Crystal violet) |
E Param.: -11.26 | | J. Am. Chem. Soc. 2003, 125, 286-295 10.1021/ja021010y |