C-Electrophiles
Name | Solvent |
Reactivity Parameters |
Classification |
Reference (title or year) |
---|---|---|---|---|
(E)-N-benzylidene-4-methylbenzenesulfonamide (in DMSO) | DMSO | E Param.: -11.50 | J. Am. Chem. Soc. 2011, 133, 8240-8251 10.1021/ja200820m | |
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-(p-methoxybenzylidene)-indan-1,3-dione | E Param.: -11.32 | Org. Biomol. Chem. 2007, 5, 3020-3026 10.1039/b708025e | ||
maleic anhydride | DMSO | E Param.: -11.31 | Eur. J. Org. Chem. 2014, , 2956-2963 10.1002/ejoc.201301779 | |
(4-NMe2)3-tritylium ion (= Crystal violet) | E Param.: -11.26 | J. Am. Chem. Soc. 2003, 125, 286-295 10.1021/ja021010y | ||
dicarbonyl(cyclopentadienyl)propene-iron(II) | E Param.: -11.20 | Helv. Chim. Acta 2005, 88, 1754-1768 10.1002/hlca.200590137 | ||
p-fluoranil (C-F) | E Param.: -11.12 | J. Am. Chem. Soc. 2014, 136, 11499-11512 10.1021/ja505613b | ||
p-(methoxy)benzylidenemalononitrile | E Param.: -10.80 | J. Org. Chem. 2003, 68, 6880-6886 10.1021/jo0344182 | ||
dma(S)BBS | E Param.: -10.73 | J. Org. Chem. 2007, 72, 9170-9180 10.1021/jo071273g | ||
p-AniCH=N+Me2 (in MeCN) | MeCN | E Param.: -10.69 | J. Am. Chem. Soc. 2013, 135, 6579-6587 10.1021/ja401106x | |
(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 | |
aniBBS | E Param.: -10.37 | J. Org. Chem. 2007, 72, 9170-9180 10.1021/jo071273g | ||
pipN+=CH-CH-Ph | E Param.: -10.30 | Angew. Chem. Int. Ed. 2008, 47, 8723-8726 10.1002/anie.200802889 | ||
(4-NMe2)2-tritylium ion (= Malachite green) | E Param.: -10.29 | J. Am. Chem. Soc. 2003, 125, 286-295 10.1021/ja021010y | ||
p-(methoxy)benzylidene Meldrum's acid | E Param.: -10.28 | J. Org. Chem. 2008, 73, 2738-2745 10.1021/jo702590s | ||
bis(1,2-dimethylindol-3-yl)methylium ion | E Param.: -10.23 | J. Org. Chem. 2015, 80, 8643-8656 10.1021/acs.joc.5b01298 | ||
Pd-allyl cation | E Param.: -10.11 | Acc. Chem. Res. 2003, 36, 66-77 10.1021/ar020094c | ||
2-benzylidene-indan-1,3-dione | E Param.: -10.11 | Org. Biomol. Chem. 2007, 5, 3020-3026 10.1039/b708025e | ||
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[...] | |
(lil)2CH+ | E Param.: -10.04 | J. Am. Chem. Soc. 2001, 123, 9500-9512 10.1021/ja010890y | ||
1,1,3-tris(4-(dimethylamino)phenyl)allylium ion | E Param.: -9.84 | Acc. Chem. Res. 2003, 36, 66-77 10.1021/ar020094c | ||
pyrN+=CH-CH-Ph | E Param.: -9.80 | Angew. Chem. Int. Ed. 2008, 47, 8723-8726 10.1002/anie.200802889 | ||
bis(julidin-9-yl)allylium ion | E Param.: -9.78 | J. Org. Chem. 2011, 76, 9391-9408 10.1021/jo201668w | ||
pTolCH=N+CH2 (in MeCN) | MeCN | E Param.: -9.64 | J. Am. Chem. Soc. 2013, 135, 6579-6587 10.1021/ja401106x | |
PhCH=N+(CH2)5 (in MeCN) | MeCN | E Param.: -9.60 | J. Am. Chem. Soc. 2013, 135, 6579-6587 10.1021/ja401106x | |
indolecarboxylate derived iminium ion | dichloromethane | E Param.: -9.50 | Angew. Chem. Int. Ed. 2009, 48, 5034-5037 10.1002/anie.200900933 | |
(jul)2CH+ | E Param.: -9.45 | J. Am. Chem. Soc. 2001, 123, 9500-9512 10.1021/ja010890y | ||
benzylidenemalononitrile | E Param.: -9.42 | J. Org. Chem. 2003, 68, 6880-6886 10.1021/jo0344182 | ||
p-fluoranil (C=O) | E Param.: -9.37 | J. Am. Chem. Soc. 2014, 136, 11499-11512 10.1021/ja505613b | ||
PhCH=N+(CH2)4 (in MeCN) | MeCN | E Param.: -9.35 | J. Am. Chem. Soc. 2013, 135, 6579-6587 10.1021/ja401106x | |
PhCH=N+Me2 (in MeCN) | MeCN | E Param.: -9.27 | J. Am. Chem. Soc. 2013, 135, 6579-6587 10.1021/ja401106x | |
C7H9+-Fe(CO)3 | E Param.: -9.21 | 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 | ||
benzylidene-Meldrum's acid | E Param.: -9.15 | J. Org. Chem. 2008, 73, 2738-2745 10.1021/jo702590s | ||
6-nitro-tetrazolo[1,5a]pyridine | E Param.: -9.05 | J. Org. Chem. 2005, 70, 6242-6253 10.1021/jo0505526 | ||
1,1-bis(4-dimethylaminophenyl)-3-phenylallylium ion | E Param.: -8.97 | Acc. Chem. Res. 2003, 36, 66-77 10.1021/ar020094c | ||
C6H6OMe+-Fe(CO)3 | E Param.: -8.94 | Acc. Chem. Res. 2003, 36, 66-77 10.1021/ar020094c | ||
o-chloranil (C=O) | E Param.: -8.77 | J. Am. Chem. Soc. 2014, 136, 11499-11512 10.1021/ja505613b | ||
(ind)2CH+ | E Param.: -8.76 | J. Am. Chem. Soc. 2001, 123, 9500-9512 10.1021/ja010890y | ||
ani(Br)2QM | E Param.: -8.63 | Angew. Chem. Int. Ed. 2002, 41, 91-95 10.1002/1521-3773(20[...] | ||
mor iminium | E Param.: -8.60 | Angew. Chem. Int. Ed. 2008, 47, 8723-8726 10.1002/anie.200802889 | ||
fc2CH+ | E Param.: -8.54 | Acc. Chem. Res. 2003, 36, 66-77 10.1021/ar020094c | ||
(PhCH2)2N+=CH-CH-Ph | E Param.: -8.50 | Angew. Chem. Int. Ed. 2008, 47, 8723-8726 10.1002/anie.200802889 | ||
5-methoxyfuroxano[3,4-d]pyrimidine | E Param.: -8.37 | J. Phys. Org. Chem. 2003, 16, 431-437 10.1002/poc.606 | ||
p-CF3-C6H4-CH=N+Me2 (in MeCN) | MeCN | E Param.: -8.34 | J. Am. Chem. Soc. 2013, 135, 6579-6587 10.1021/ja401106x | |
(thq)2CH+ | E Param.: -8.22 | J. Am. Chem. Soc. 2001, 123, 9500-9512 10.1021/ja010890y | ||
Jorgensen/Hayashi-iminium ion | E Param.: -8.20 | Angew. Chem. Int. Ed. 2008, 47, 8723-8726 10.1002/anie.200802889 | ||
(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 | |
(4-NMe2)-tritylium ion | E Param.: -7.93 | J. Am. Chem. Soc. 2003, 125, 286-295 10.1021/ja021010y | ||
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 |