C-Nucleophiles
| Name | Solvent |
Reactivity Parameters |
Classification |
Reference (title or year) |
|---|---|---|---|---|
anion of Meldrum's acid (in water)   |
water | N Param.: 12.06 sN Param.: 0.66 |
 |
J. Am. Chem. Soc. 2003, 125, 12980-12986 10.1021/ja036838e |
anion of dimedone (in water)  |
water | N Param.: 11.77 sN Param.: 0.63 |
|
J. Am. Chem. Soc. 2003, 125, 12980-12986 10.1021/ja036838e |
anion of acetylacetone (in water)  |
water | N Param.: 13.73 sN Param.: 0.64 |
|
J. Am. Chem. Soc. 2003, 125, 12980-12986 10.1021/ja036838e |
anion of ethyl acetylacetate (in water)  |
water | N Param.: 15.99 sN Param.: 0.62 |
|
J. Am. Chem. Soc. 2003, 125, 12980-12986 10.1021/ja036838e |
anion of malononitrile (in water)  |
water | N Param.: 19.50 sN Param.: 0.55 |
|
J. Am. Chem. Soc. 2003, 125, 12980-12986 10.1021/ja036838e |
anion of ethyl cyanoacetate (in water)  |
water | N Param.: 15.57 sN Param.: 0.58 |
|
J. Am. Chem. Soc. 2003, 125, 12980-12986 10.1021/ja036838e |
anion of diethyl malonate (in water)  |
water | N Param.: 16.15 sN Param.: 0.66 |
|
J. Am. Chem. Soc. 2003, 125, 12980-12986 10.1021/ja036838e |
anion of diethyl methylmalonate (in water)  |
water | N Param.: 17.68 sN Param.: 0.50 |
|
J. Am. Chem. Soc. 2003, 125, 12980-12986 10.1021/ja036838e |
anion of 3-methyl acetylacetone (in water)  |
water | N Param.: 14.33 sN Param.: 0.69 |
|
J. Am. Chem. Soc. 2003, 125, 12980-12986 10.1021/ja036838e |
anion of nitroethane (in water)  |
water | N Param.: 11.25 sN Param.: 0.52 |
|
J. Org. Chem. 2004, 69, 7565-7576 10.1021/jo048773j |
anion of nitromethane (in water)  |
water | N Param.: 12.06 sN Param.: 0.53 |
|
J. Org. Chem. 2004, 69, 7565-7576 10.1021/jo048773j |
anion of 2-nitropropane (in water)  |
water | N Param.: 10.69 sN Param.: 0.56 |
|
J. Org. Chem. 2004, 69, 7565-7576 10.1021/jo048773j |
anion of phenylnitromethane (in H2O)  |
water | N Param.: 12.05 sN Param.: 0.53 |
|
J. Org. Chem. 2004, 69, 7565-7576 10.1021/jo048773j |
anion of p-tolylnitromethane (in water)  |
water | N Param.: 13.09 sN Param.: 0.50 |
|
J. Org. Chem. 2004, 69, 7565-7576 10.1021/jo048773j |
anion of (4-nitrophenyl)nitromethane (in water)  |
water | N Param.: 13.58 sN Param.: 0.52 |
|
J. Org. Chem. 2004, 69, 7565-7576 10.1021/jo048773j |
anion of (3-nitrophenyl)nitromethane (in water)  |
water | N Param.: 14.25 sN Param.: 0.46 |
|
J. Org. Chem. 2004, 69, 7565-7576 10.1021/jo048773j |
anion of (4-cyanophenyl)nitromethane (in water)  |
water | N Param.: 13.23 sN Param.: 0.52 |
|
J. Org. Chem. 2004, 69, 7565-7576 10.1021/jo048773j |
1,3-dimesityl-1H-imidazol-3-ium-2-ide (in THF)  |
THF | N Param.: 21.72 sN Param.: 0.45 |
|
Angew. Chem. Int. Ed. 2011, 50, 6915-6919 10.1002/anie.201102435 |
1,3-dimesityl-4,5-dihydro-1H-imidazol-3-ium-2-ide (in THF)  |
THF | N Param.: 23.35 sN Param.: 0.40 |
|
Angew. Chem. Int. Ed. 2011, 50, 6915-6919 10.1002/anie.201102435 |
1,3,4-triphenyl-1H-1,2,4-triazol-4-ium-5-ide (in THF)  |
THF | N Param.: 14.07 sN Param.: 0.84 |
|
Angew. Chem. Int. Ed. 2011, 50, 6915-6919 10.1002/anie.201102435 |
MeO-Breslow 1a  |
THF | N Param.: 14.77 sN Param.: 0.80 |
|
Angew. Chem. Int. Ed. 2012, 51, 10408-10412 10.1002/anie.201204524 |
MeO-Breslow 1b  |
THF | N Param.: 10.45 sN Param.: 0.81 |
|
Angew. Chem. Int. Ed. 2012, 51, 10408-10412 10.1002/anie.201204524 |
MeO-Breslow 1c  |
THF | N Param.: 16.61 sN Param.: 0.68 |
|
Angew. Chem. Int. Ed. 2012, 51, 10408-10412 10.1002/anie.201204524 |
MeO-Breslow 1e  |
THF | N Param.: 15.65 sN Param.: 0.52 |
|
Angew. Chem. Int. Ed. 2012, 51, 10408-10412 10.1002/anie.201204524 |
Dexoxy Breslow intermediate 6  |
THF | N Param.: 15.58 sN Param.: 0.57 |
|
Angew. Chem. Int. Ed. 2012, 51, 10408-10412 10.1002/anie.201204524 |
Desoxy Breslow intermediate 2a  |
THF | N Param.: 17.12 sN Param.: 0.80 |
|
Angew. Chem. Int. Ed. 2012, 51, 6231-6235 10.1002/anie.201202327 |
Desoxy Breslow intermediate 2a'  |
THF | N Param.: 14.45 sN Param.: 0.71 |
|
Angew. Chem. Int. Ed. 2012, 51, 6231-6235 10.1002/anie.201202327 |
Desoxy Breslow intermediate 2b  |
THF | N Param.: 13.91 sN Param.: 0.64 |
|
Angew. Chem. Int. Ed. 2012, 51, 6231-6235 10.1002/anie.201202327 |
Desoxy Breslow intermediate 2b'  |
THF | N Param.: 11.42 sN Param.: 0.70 |
|
Angew. Chem. Int. Ed. 2012, 51, 6231-6235 10.1002/anie.201202327 |
Desoxy Breslow intermediate 2c'  |
THF | N Param.: 12.75 sN Param.: 0.71 |
|
Angew. Chem. Int. Ed. 2012, 51, 6231-6235 10.1002/anie.201202327 |
(Z)-1-(1,3-dimesityl-1H-imidazol-3-ium-2-yl)-2-phenylprop-1-en-1-olate (in THF)  |
THF | N Param.: 15.33 sN Param.: 0.79 |
|
Angew. Chem. Int. Ed. 2013, 52, 11163-11167 10.1002/ange.201303524 |
(Z)-1-(1,3-dimesityl-4,5-dihydro-1H-imidazol-3-ium-2-yl)-2-phenylprop-1-en-1-olate (in THF)  |
THF | N Param.: 15.92 sN Param.: 0.72 |
|
Angew. Chem. Int. Ed. 2013, 52, 11163-11167 10.1002/ange.201303524 |
(Z)-2-phenyl-1-(1,3,4-triphenyl-4H-1,2,4-triazol-1-ium-5-yl)prop-1-en-1-olate (in THF)  |
THF | N Param.: 14.40 sN Param.: 0.66 |
|
Angew. Chem. Int. Ed. 2013, 52, 11163-11167 10.1002/ange.201303524 |
3-mesityl-1-methyl-1H-imidazol-3-ium-2-ide (in THF)  |
THF | N Param.: 21.50 sN Param.: 0.45 |
|
Org. Lett. 2016, 18, 3566-3569 10.1021/acs.orglett.[...] |
3-(tert-butyl)-1-methyl-1H-imidazol-3-ium-2-ide (in THF)  |
THF | N Param.: 16.54 sN Param.: 0.47 |
|
Org. Lett. 2016, 18, 3566-3569 10.1021/acs.orglett.[...] |
3-(4-methoxyphenyl)-1-methyl-1H-imidazol-3-ium-2-ide (in THF)  |
THF | N Param.: 20.41 sN Param.: 0.46 |
|
Org. Lett. 2016, 18, 3566-3569 10.1021/acs.orglett.[...] |
3-(2,6-dimethoxyphenyl)-1-methyl-1H-imidazol-3-ium-2-ide (in THF)  |
THF | N Param.: 23.00 sN Param.: 0.46 |
|
Org. Lett. 2016, 18, 3566-3569 10.1021/acs.orglett.[...] |
1,3-dimethyl-2-methyleneimidazolidine (in THF)  |
THF | N Param.: 18.11 sN Param.: 0.68 |
|
J. Org. Chem. 2021, 86, 2974-2985 10.1021/acs.joc.0c02838 |
1,3-dimethyl-2-methylenehexahydropyrimidine (in THF)  |
THF | N Param.: 18.68 sN Param.: 0.63 |
|
J. Org. Chem. 2021, 86, 2974-2985 10.1021/acs.joc.0c02838 |
1,3-dimesityl-2-methylene-2,3-dihydro-1H-imidazole (in THF)  |
THF | N Param.: 17.80 sN Param.: 0.79 |
|
J. Org. Chem. 2021, 86, 2974-2985 10.1021/acs.joc.0c02838 |
1,3-dimethyl-2-methylene-2,3-dihydro-1H-benzo[d]imidazole  |
THF | N Param.: 19.84 sN Param.: 0.58 |
|
J. Org. Chem. 2021, 86, 2974-2985 10.1021/acs.joc.0c02838 |
1,3-Bis(2,6-diisopropylphenyl)-5-methylene-4-(2,4,6-triisopropylphenyl)-4,5-dihydro-1H-1,2,3-triazol-3-ium-4-ide (in THF)  |
THF | N Param.: 21.36 sN Param.: 0.42 |
|
Angew. Chem. Int. Ed. 2023, 62, e202309790 10.1002/anie.202309790 |
1,3-Bis(2,6-diisopropylphenyl)-4-methylene-5-(4-(trifluoromethyl)phenyl)-4,5-dihydro-1H-1,2,3-triazol-3-ium-5-ide (in THF)  |
THF | N Param.: 22.30 sN Param.: 0.49 |
|
Angew. Chem. Int. Ed. 2023, 62, e202309790 10.1002/anie.202309790 |
1,3-Bis(2,6-diisopropylphenyl)-5-(4-methoxyphenyl)-4-methylene-4,5-dihydro-1H-1,2,3-triazol-3-ium-5-ide (in THF)  |
THF | N Param.: 23.55 sN Param.: 0.56 |
|
Angew. Chem. Int. Ed. 2023, 62, e202309790 10.1002/anie.202309790 |
1,3-Bis(2,6-diisopropylphenyl)-5-methylene-4-(2,4,6-triisopropylphenyl)-4,5-dihydro-1H-1,2,3-triazol-3-ium-4-ide (in THF)  |
THF | N Param.: 20.78 sN Param.: 0.61 |
|
Angew. Chem. Int. Ed. 2023, 62, e202309790 10.1002/anie.202309790 |
1,3-Diisopropyl-4-methylene-5-phenyl-4,5-dihydro-1H-1,2,3-triazol-3-ium-5-ide (in THF)  |
THF | N Param.: 30.25 sN Param.: 0.54 |
|
Angew. Chem. Int. Ed. 2023, 62, e202309790 10.1002/anie.202309790 |
5-(tert-Butyl)-1,3-diisopropyl-4-methylene-4,5-dihydro-1H-1,2,3-triazol-3-ium-5-ide (in THF)  |
THF | N Param.: 31.92 sN Param.: 0.52 |
|
Angew. Chem. Int. Ed. 2023, 62, e202309790 10.1002/anie.202309790 |
1,3-bis(2,6-diisopropylphenyl)-4-methylene-5-phenyl-4,5-dihydro-1H-1,2,3-triazol-3-ium-5-ide (in THF)  |
THF | N Param.: 22.80 sN Param.: 0.60 |
|
Angew. Chem. Int. Ed. 2023, 62, e202309790 10.1002/anie.202309790 |
1,3-bis(2,6-diisopropylphenyl)-5-methyl-4-methylene-4,5-dihydro-1H-1,2,3-triazol-3-ium-5-ide (in THF)  |
THF | N Param.: 24.86 sN Param.: 0.52 |
|
Angew. Chem. Int. Ed. 2023, 62, e202309790 10.1002/anie.202309790 |
1-mesityl-3-methyl-5-methylene-2,4,6-triphenyl-2,5-dihydropyridin-1-ium-2-ide (in THF)  |
THF | N Param.: 26.16 sN Param.: 0.52 |
|
Angew. Chem. Int. Ed. 2024, , e202318283 10.1002/anie.202318283 |