C-Nucleophiles

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Name	Solvent	Reactivity Parameters	Reference (title or year)
(E)-13-(ethylthio)-6-styryl-6,12-diazadispiro[4.1.47.25]tridec-12-ene (in MeCN)	MeCN	N Param.: 7.79 s_N 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 s_N 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 s_N 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 s_N Param.: 0.84	Chem. Eur. J. 2024, 30, e202302764 10.1002/chem.202302764
diazocyclopentadiene (in CH2Cl2)	dichloromethane	N Param.: 4.84 s_N Param.: 1.06	Synthesis 2023, 55, 354-358 10.1055/s-0041-1737327
(E)-2,2,3,5,5-pentamethyl-1-styrylimidazolidin-4-one (in MeCN)	MeCN	N Param.: 7.10 s_N 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 s_N 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 s_N 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 s_N 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 s_N Param.: 0.52	Angew. Chem. Int. Ed. 2024, , e202318283 10.1002/anie.202318283
anion of nitroethane (in DMF)	DMF	N Param.: 22.21 s_N Param.: 0.48	Chem. Eur. J. 2008, 14, 6108-6118 10.1002/chem.200800329
chloro(phenylsulfonyl)methanide (in DMF)	DMF	N Param.: 26.64 s_N Param.: 0.64	Chem. Eur. J. 2008, 14, 6108-6118 10.1002/chem.200800329
1,3,5-trimethyl-2-methylene-1,2-dihydropyridine (in DMSO)	DMSO	N Param.: 21.16 s_N 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 s_N 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 s_N 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 s_N 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 s_N 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 s_N 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 s_N 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 s_N Param.: 0.75	J. Org. Chem. 2024, 89, 6915-6928 10.1021/acs.joc.4c00277
methyl diazoacetate	dichloromethane	N Param.: 4.68 s_N Param.: 0.94	J. Am. Chem. Soc. 2023, 145, 7416-7434 10.1021/jacs.2c13872
dimethyl diazomalonate	dichloromethane	N Param.: -1.24 s_N Param.: 0.81	J. Am. Chem. Soc. 2023, 145, 7416-7434 10.1021/jacs.2c13872
(1-azidovinyl)benzene	dichloromethane	N Param.: 4.57 s_N Param.: 0.94	Chem. Commun. 2026, 62, 5041-5045 10.1039/d6cc00190d
1-(1-azidovinyl)-4-methylbenzene	dichloromethane	N Param.: 5.47 s_N Param.: 0.87	Chem. Commun. 2026, 62, 5041-5045 10.1039/d6cc00190d
1-(1-azidovinyl)-4-methoxybenzene	dichloromethane	N Param.: 6.08 s_N Param.: 0.99	Chem. Commun. 2026, 62, 5041-5045 10.1039/d6cc00190d
4-(1-azidovinyl)-1,1'-biphenyl	dichloromethane	N Param.: 5.17 s_N Param.: 0.86	Chem. Commun. 2026, 62, 5041-5045 10.1039/d6cc00190d
1-(1-azidovinyl)-4-(chloromethyl)benzene	dichloromethane	N Param.: 4.13 s_N Param.: 0.96	Chem. Commun. 2026, 62, 5041-5045 10.1039/d6cc00190d
1-(1-azidovinyl)-4-(trifluoromethyl)benzene	dichloromethane	N Param.: 3.10 s_N Param.: 0.77	Chem. Commun. 2026, 62, 5041-5045 10.1039/d6cc00190d
2-(1-azidovinyl)naphthalene	dichloromethane	N Param.: 5.39 s_N Param.: 0.89	Chem. Commun. 2026, 62, 5041-5045 10.1039/d6cc00190d
1-(1-azidovinyl)naphthalene	dichloromethane	N Param.: 3.17 s_N Param.: 0.88	Chem. Commun. 2026, 62, 5041-5045 10.1039/d6cc00190d
2,3-dihydrofuran (in MeCN)	MeCN	N Param.: 5.02 s_N Param.: 0.63	Angew. Chem. Int. Ed. 2026, 65, e24329 10.1002/anie.202524329
5-methyl-2,3-dihydrofuran (in MeCN)	MeCN	N Param.: 7.65 s_N Param.: 0.86	Angew. Chem. Int. Ed. 2026, 65, e24329 10.1002/anie.202524329
(4,5-dihydrofuran-2-yl)trimethylsilane (in MeCN)	MeCN	N Param.: 4.23 s_N Param.: 0.90	Angew. Chem. Int. Ed. 2026, 65, e24329 10.1002/anie.202524329
3,4-dihydro-2H-pyran (in MeCN)	MeCN	N Param.: 2.98 s_N Param.: 0.72	Angew. Chem. Int. Ed. 2026, 65, e24329 10.1002/anie.202524329
(3,4-dihydro-2H-pyran-6-yl)trimethylsilane (in MeCN)	MeCN	N Param.: 2.87 s_N Param.: 0.68	Angew. Chem. Int. Ed. 2026, 65, e24329 10.1002/anie.202524329
((3,4-dihydro-2H-pyran-6-yl)methoxy)triisopropylsilane (in MeCN)	MeCN	N Param.: 2.87 s_N Param.: 0.66	Angew. Chem. Int. Ed. 2026, 65, e24329 10.1002/anie.202524329
6-((benzyloxy)methyl)-3,4-dihydro-2H-pyran (in MeCN)	MeCN	N Param.: 2.81 s_N Param.: 0.57	Angew. Chem. Int. Ed. 2026, 65, e24329 10.1002/anie.202524329
N-Boc-2,3-dihydro-1H-pyrrole (in MeCN)	MeCN	N Param.: 6.82 s_N Param.: 1.24	Angew. Chem. Int. Ed. 2026, 65, e24329 10.1002/anie.202524329
3,4-dimethoxy-2-(methoxymethyl)-3,4-dihydro-2H-pyran	dichloromethane	N Param.: 1.53 s_N Param.: 1.38	Angew. Chem. Int. Ed. 2026, 65, e24329 10.1002/anie.202524329
2-(acetoxymethyl)-3,4-dihydro-2H-pyran-3,4-diyl diacetate	dichloromethane	N Param.: 1.72 s_N Param.: 1.24	Angew. Chem. Int. Ed. 2026, 65, e24329 10.1002/anie.202524329
3,4-bis(benzyloxy)-2-((benzyloxy)methyl)-3,4-dihydro-2H-pyran	dichloromethane	N Param.: 1.89 s_N Param.: 1.27	Angew. Chem. Int. Ed. 2026, 65, e24329 10.1002/anie.202524329
2-((TBDMSO-methyl)-3,4-bis(TBDMSO)-3,4-dihydro-2H-pyran	dichloromethane	N Param.: 1.97 s_N Param.: 1.20	Angew. Chem. Int. Ed. 2026, 65, e24329 10.1002/anie.202524329
3,4-bis(benzyloxy)-2-((benzyloxy)methyl)-6-methyl-3,4-dihydro-2H-pyran	dichloromethane	N Param.: 4.98 s_N Param.: 0.65	Angew. Chem. Int. Ed. 2026, 65, e24329 10.1002/anie.202524329
3,4-bis(benzyloxy)-2-((benzyloxy)methyl)-3,4-dihydro-2H-pyran	dichloromethane	N Param.: 1.75 s_N Param.: 1.37	Angew. Chem. Int. Ed. 2026, 65, e24329 10.1002/anie.202524329
3,4-bis(benzyloxy)-2-((benzyloxy)methyl)-6-methylenetetrahydro-2H-pyran	dichloromethane	N Param.: 6.19 s_N Param.: 0.79	Angew. Chem. Int. Ed. 2026, 65, 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 s_N Param.: 1.28	Angew. Chem. Int. Ed. 2026, 65, e24329 10.1002/anie.202524329
3,4,5-tris(benzyloxy)-2-((benzyloxy)methyl)-6-methylenetetrahydro-2H-pyran	dichloromethane	N Param.: 4.01 s_N Param.: 0.91	Angew. Chem. Int. Ed. 2026, 65, e24329 10.1002/anie.202524329
3,4-bis(benzyloxy)-2-((benzyloxy)methyl)-5-methylenetetrahydrofuran	dichloromethane	N Param.: 5.50 s_N Param.: 0.76	Angew. Chem. Int. Ed. 2026, 65, e24329 10.1002/anie.202524329
4-((benzyloxy)methyl)-2,2-dimethyl-6-methylenetetrahydrofuro[3,4-d][1,3]dioxole	dichloromethane	N Param.: 5.35 s_N Param.: 0.88	Angew. Chem. Int. Ed. 2026, 65, 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 s_N Param.: 1.24	Angew. Chem. Int. Ed. 2026, 65, e24329 10.1002/anie.202524329