C-Nucleophiles
| Name | Solvent |
Reactivity Parameters |
Classification |
Reference (title or year) |
|---|---|---|---|---|
diazocyclopentadiene (in CH2Cl2)![]() ![]() |
dichloromethane | N Param.: 4.84 sN Param.: 1.06 | Synthesis 2023, 55, 354-358 10.1055/s-0041-1737327 | |
methyl diazoacetate![]() ![]() |
dichloromethane | N Param.: 4.68 sN Param.: 0.94 | J. Am. Chem. Soc. 2023, 145, 7416-7434 10.1021/jacs.2c13872 | |
dimethyl diazomalonate![]() ![]() |
dichloromethane | N Param.: -1.24 sN Param.: 0.81 | J. Am. Chem. Soc. 2023, 145, 7416-7434 10.1021/jacs.2c13872 | |
(E)-2-((1-(but-1-en-1-yl)-2,2,5,5-tetramethyl-2,5-dihydro-1H-imidazol-4-yl)thio)acetonitrile (in MeCN)![]() ![]() |
MeCN | N Param.: 9.23 sN Param.: 0.74 | Chem. Eur. J. 2024, 30, e202302764 10.1002/chem.202302764 | |
(E)-4-(ethylthio)-2,2,5,5-tetramethyl-1-styryl-2,5-dihydro-1H-imidazole (in MeCN)![]() ![]() |
MeCN | N Param.: 8.12 sN Param.: 0.88 | Chem. Eur. J. 2024, 30, e202302764 10.1002/chem.202302764 | |
(E)-13-(ethylthio)-6-styryl-6,12-diazadispiro[4.1.47.25]tridec-12-ene (in MeCN)![]() ![]() |
MeCN | N Param.: 7.79 sN Param.: 0.87 | Chem. Eur. J. 2024, 30, e202302764 10.1002/chem.202302764 | |
(E)-4-(ethylthio)-2,2,5,5-tetramethyl-1-(3-phenylprop-1-en-1-yl)-2,5-dihydro-1H-imidazole (in MeCN)![]() ![]() |
MeCN | N Param.: 9.64 sN Param.: 0.70 | Chem. Eur. J. 2024, 30, e202302764 10.1002/chem.202302764 | |
(E)-4-(ethylthio)-2,2,5,5-tetramethyl-1-(3-phenylbut-1-en-1-yl)-2,5-dihydro-1H-imidazole (in MeCN)![]() ![]() |
MeCN | N Param.: 7.92 sN Param.: 0.73 | Chem. Eur. J. 2024, 30, e202302764 10.1002/chem.202302764 | |
(E)-4-(benzylthio)-2,2,5,5-tetramethyl-1-styryl-2,5-dihydro-1H-imidazole (in MeCN)![]() ![]() |
MeCN | N Param.: 8.30 sN Param.: 0.84 | Chem. Eur. J. 2024, 30, e202302764 10.1002/chem.202302764 | |
(E)-2,2,3,5,5-pentamethyl-1-styrylimidazolidin-4-one (in MeCN)![]() ![]() |
MeCN | N Param.: 7.10 sN Param.: 0.82 | Chem. Eur. J. 2024, 30, e202302764 10.1002/chem.202302764 | |
(E)-2,2,3,5,5-pentamethyl-1-styrylimidazolidine-4-thione (in MeCN)![]() ![]() |
MeCN | N Param.: 6.49 sN Param.: 0.83 | Chem. Eur. J. 2024, 30, e202302764 10.1002/chem.202302764 | |
(E)-4-(ethylthio)-2,2,5,5-tetramethyl-1-styryl-2,5-dihydro-1H-imidazole (in CH2Cl2)![]() ![]() |
dichloromethane | N Param.: 8.13 sN Param.: 0.97 | Chem. Eur. J. 2024, 30, e202302764 10.1002/chem.202302764 | |
(E)-4-(benzylthio)-2,2,5,5-tetramethyl-1-styryl-2,5-dihydro-1H-imidazole (in CH2Cl2)![]() ![]() |
dichloromethane | N Param.: 7.99 sN Param.: 0.98 | Chem. Eur. J. 2024, 30, e202302764 10.1002/chem.202302764 | |
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 | |
1,3,5-trimethyl-2-methylene-1,2-dihydropyridine (in DMSO)![]() ![]() |
DMSO | N Param.: 21.16 sN Param.: 0.59 | Eur. J. Org. Chem. 2024, 27, e202400373 10.1002/ejoc.202400373 | |
1,3-dimethyl-2-methylene-1,2-dihydropyridine (in DMSO)![]() ![]() |
DMSO | N Param.: 19.91 sN Param.: 0.62 | Eur. J. Org. Chem. 2024, 27, e202400373 10.1002/ejoc.202400373 | |
1,3-dimethyl-2-methylene-1,2-dihydropyridine (in MeCN)![]() ![]() |
MeCN | N Param.: 19.69 sN Param.: 0.61 | Eur. J. Org. Chem. 2024, 27, e202400373 10.1002/ejoc.202400373 | |
1,6-dimethyl-2-methylene-1,2-dihydropyridine (in DMSO)![]() ![]() |
DMSO | N Param.: 20.76 sN Param.: 0.60 | Eur. J. Org. Chem. 2024, 27, e202400373 10.1002/ejoc.202400373 | |
1-methyl-2-methylene-3-phenyl-1,2-dihydropyridine (in DMSO)![]() ![]() |
DMSO | N Param.: 19.41 sN Param.: 0.61 | Eur. J. Org. Chem. 2024, 27, e202400373 10.1002/ejoc.202400373 | |
1-(4-(tert-butyl)phenyl)-2-methylene-4,6-diphenyl-1,2-dihydropyridine (in DMSO)![]() ![]() |
DMSO | N Param.: 19.36 sN Param.: 0.68 | Eur. J. Org. Chem. 2024, 27, e202400373 10.1002/ejoc.202400373 | |
enolate of 3-isochromanone (in DMSO)![]() ![]() |
DMSO | N Param.: 25.39 sN Param.: 0.54 | J. Org. Chem. 2024, 89, 6915-6928 10.1021/acs.joc.4c00277 | |
enolate of 2-coumaranone (in DMSO)![]() ![]() |
DMSO | N Param.: 19.60 sN Param.: 0.75 | J. Org. Chem. 2024, 89, 6915-6928 10.1021/acs.joc.4c00277 | |
(1-azidovinyl)benzene![]() ![]() |
dichloromethane | N Param.: 4.57 sN Param.: 0.94 | Chem. Commun. 2026, 62, 5041-5045 10.1039/d6cc00190d | |
1-(1-azidovinyl)-4-methylbenzene![]() ![]() |
dichloromethane | N Param.: 5.47 sN Param.: 0.87 | Chem. Commun. 2026, 62, 5041-5045 10.1039/d6cc00190d | |
1-(1-azidovinyl)-4-methoxybenzene![]() ![]() |
dichloromethane | N Param.: 6.08 sN Param.: 0.99 | Chem. Commun. 2026, 62, 5041-5045 10.1039/d6cc00190d | |
4-(1-azidovinyl)-1,1'-biphenyl![]() ![]() |
dichloromethane | N Param.: 5.17 sN Param.: 0.86 | Chem. Commun. 2026, 62, 5041-5045 10.1039/d6cc00190d | |
1-(1-azidovinyl)-4-(chloromethyl)benzene![]() ![]() |
dichloromethane | N Param.: 4.13 sN Param.: 0.96 | Chem. Commun. 2026, 62, 5041-5045 10.1039/d6cc00190d | |
1-(1-azidovinyl)-4-(trifluoromethyl)benzene![]() ![]() |
dichloromethane | N Param.: 3.10 sN Param.: 0.77 | Chem. Commun. 2026, 62, 5041-5045 10.1039/d6cc00190d | |
2-(1-azidovinyl)naphthalene![]() ![]() |
dichloromethane | N Param.: 5.39 sN Param.: 0.89 | Chem. Commun. 2026, 62, 5041-5045 10.1039/d6cc00190d | |
1-(1-azidovinyl)naphthalene![]() ![]() |
dichloromethane | N Param.: 3.17 sN Param.: 0.88 | Chem. Commun. 2026, 62, 5041-5045 10.1039/d6cc00190d | |
2,3-dihydrofuran (in MeCN)![]() ![]() |
MeCN | N Param.: 5.02 sN Param.: 0.63 | Angew. Chem. Int. Ed. 2026, EarlyView, e24329 10.1002/anie.202524329 | |
5-methyl-2,3-dihydrofuran (in MeCN)![]() ![]() |
MeCN | N Param.: 7.65 sN Param.: 0.86 | Angew. Chem. Int. Ed. 2026, EarlyView, e24329 10.1002/anie.202524329 | |
(4,5-dihydrofuran-2-yl)trimethylsilane (in MeCN)![]() ![]() |
MeCN | N Param.: 4.23 sN Param.: 0.90 | Angew. Chem. Int. Ed. 2026, EarlyView, e24329 10.1002/anie.202524329 | |
3,4-dihydro-2H-pyran (in MeCN)![]() ![]() |
MeCN | N Param.: 2.98 sN Param.: 0.72 | Angew. Chem. Int. Ed. 2026, EarlyView, e24329 10.1002/anie.202524329 | |
(3,4-dihydro-2H-pyran-6-yl)trimethylsilane (in MeCN)![]() ![]() |
MeCN | N Param.: 2.87 sN Param.: 0.68 | Angew. Chem. Int. Ed. 2026, EarlyView, e24329 10.1002/anie.202524329 | |
((3,4-dihydro-2H-pyran-6-yl)methoxy)triisopropylsilane (in MeCN)![]() ![]() |
MeCN | N Param.: 2.87 sN Param.: 0.66 | Angew. Chem. Int. Ed. 2026, EarlyView, e24329 10.1002/anie.202524329 | |
6-((benzyloxy)methyl)-3,4-dihydro-2H-pyran (in MeCN)![]() ![]() |
MeCN | N Param.: 2.81 sN Param.: 0.57 | Angew. Chem. Int. Ed. 2026, EarlyView, e24329 10.1002/anie.202524329 | |
N-Boc-2,3-dihydro-1H-pyrrole (in MeCN)![]() ![]() |
MeCN | N Param.: 6.82 sN Param.: 1.24 | Angew. Chem. Int. Ed. 2026, EarlyView, e24329 10.1002/anie.202524329 | |
3,4-dimethoxy-2-(methoxymethyl)-3,4-dihydro-2H-pyran![]() ![]() |
dichloromethane | N Param.: 1.53 sN Param.: 1.38 | Angew. Chem. Int. Ed. 2026, EarlyView, e24329 10.1002/anie.202524329 | |
2-(acetoxymethyl)-3,4-dihydro-2H-pyran-3,4-diyl diacetate![]() ![]() |
dichloromethane | N Param.: 1.72 sN Param.: 1.24 | Angew. Chem. Int. Ed. 2026, EarlyView, e24329 10.1002/anie.202524329 | |
3,4-bis(benzyloxy)-2-((benzyloxy)methyl)-3,4-dihydro-2H-pyran![]() ![]() |
dichloromethane | N Param.: 1.89 sN Param.: 1.27 | Angew. Chem. Int. Ed. 2026, EarlyView, e24329 10.1002/anie.202524329 | |
2-((TBDMSO-methyl)-3,4-bis(TBDMSO)-3,4-dihydro-2H-pyran![]() ![]() |
dichloromethane | N Param.: 1.97 sN Param.: 1.20 | Angew. Chem. Int. Ed. 2026, EarlyView, e24329 10.1002/anie.202524329 | |
3,4-bis(benzyloxy)-2-((benzyloxy)methyl)-6-methyl-3,4-dihydro-2H-pyran![]() ![]() |
dichloromethane | N Param.: 4.98 sN Param.: 0.65 | Angew. Chem. Int. Ed. 2026, EarlyView, e24329 10.1002/anie.202524329 | |
3,4-bis(benzyloxy)-2-((benzyloxy)methyl)-3,4-dihydro-2H-pyran![]() ![]() |
dichloromethane | N Param.: 1.75 sN Param.: 1.37 | Angew. Chem. Int. Ed. 2026, EarlyView, e24329 10.1002/anie.202524329 | |
3,4-bis(benzyloxy)-2-((benzyloxy)methyl)-6-methylenetetrahydro-2H-pyran![]() ![]() |
dichloromethane | N Param.: 6.19 sN Param.: 0.79 | Angew. Chem. Int. Ed. 2026, EarlyView, e24329 10.1002/anie.202524329 | |
8-(benzyloxy)-2,2-di-tert-butyl-4,4a,8,8a-tetrahydropyrano[3,2-d][1,3,2]dioxasiline![]() ![]() |
dichloromethane | N Param.: 1.85 sN Param.: 1.28 | Angew. Chem. Int. Ed. 2026, EarlyView, e24329 10.1002/anie.202524329 | |
3,4,5-tris(benzyloxy)-2-((benzyloxy)methyl)-6-methylenetetrahydro-2H-pyran![]() ![]() |
dichloromethane | N Param.: 4.01 sN Param.: 0.91 | Angew. Chem. Int. Ed. 2026, EarlyView, e24329 10.1002/anie.202524329 | |
3,4-bis(benzyloxy)-2-((benzyloxy)methyl)-5-methylenetetrahydrofuran![]() ![]() |
dichloromethane | N Param.: 5.50 sN Param.: 0.76 | Angew. Chem. Int. Ed. 2026, EarlyView, e24329 10.1002/anie.202524329 | |
4-((benzyloxy)methyl)-2,2-dimethyl-6-methylenetetrahydrofuro[3,4-d][1,3]dioxole![]() ![]() |
dichloromethane | N Param.: 5.35 sN Param.: 0.88 | Angew. Chem. Int. Ed. 2026, EarlyView, e24329 10.1002/anie.202524329 | |
8-(benzyloxy)-2-phenyl-4,4a,8,8a-tetrahydropyrano[3,2-d][1,3]dioxine![]() ![]() |
dichloromethane | N Param.: 1.94 sN Param.: 1.24 | Angew. Chem. Int. Ed. 2026, EarlyView, e24329 10.1002/anie.202524329 |



















































