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
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, EarlyView, 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, EarlyView, 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, EarlyView, 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, EarlyView, 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, EarlyView, 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, EarlyView, 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, EarlyView, 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, EarlyView, 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, EarlyView, 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, EarlyView, 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, EarlyView, 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, 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 s_N 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 s_N 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 s_N 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 s_N 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 s_N 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 s_N 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 s_N 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 s_N Param.: 1.24	Angew. Chem. Int. Ed. 2026, EarlyView, e24329 10.1002/anie.202524329
3,4-bis(benzyloxy)-2-methyl-3,4-dihydro-2H-pyran	dichloromethane	N Param.: 2.04 s_N Param.: 1.20	Angew. Chem. Int. Ed. 2026, EarlyView, e24329 10.1002/anie.202524329
2-(1-azidovinyl)naphthalene (in Cyrene)	Cyrene (TM)	N Param.: 6.00 s_N Param.: 0.90	Chem. Commun. 2026, 62, 5041-5045 10.1039/d6cc00190d
1-butoxy-1-(trimethylsiloxy)ethene	dichloromethane	N Param.: 10.21 s_N Param.: 0.82	Eur. J. Org. Chem. 2004, , 2791-2796 10.1002/ejoc.200400134
1-butoxy-1-(t-butyl-dimethylsiloxy)ethene	dichloromethane	N Param.: 10.32 s_N Param.: 0.79	Eur. J. Org. Chem. 2004, , 2791-2796 10.1002/ejoc.200400134
1,1-bis(trimethylsiloxy)propene	dichloromethane	N Param.: 10.38 s_N Param.: 0.87	Eur. J. Org. Chem. 2004, , 2791-2796 10.1002/ejoc.200400134
1-(triphenylsiloxy)cyclopentene	dichloromethane	N Param.: 5.76 s_N Param.: 1.02	Eur. J. Org. Chem. 2005, , 1760-1764 10.1002/ejoc.200400706
2,3-dihydrofuran	dichloromethane	N Param.: 4.37 s_N Param.: 0.90	Eur. J. Org. Chem. 2005, , 1760-1764 10.1002/ejoc.200400706
toluene	dichloromethane	N Param.: -4.36 s_N Param.: 1.77	J. Am. Chem. Soc. 2012, 134, 13902-13911 10.1021/ja306522b
m-xylene	dichloromethane	N Param.: -3.57 s_N Param.: 2.08	J. Am. Chem. Soc. 2001, 123, 9500-9512 10.1021/ja010890y
(E)-propenylbenzene	dichloromethane	N Param.: -0.49 s_N Param.: 1.18	J. Am. Chem. Soc. 2012, 134, 13902-13911 10.1021/ja306522b
2-methylthiophene	dichloromethane	N Param.: 1.35 s_N Param.: 0.99	J. Am. Chem. Soc. 2012, 134, 13902-13911 10.1021/ja306522b
styrene	dichloromethane	N Param.: 0.78 s_N Param.: 0.95	J. Am. Chem. Soc. 2001, 123, 9500-9512 10.1021/ja010890y
1,3-dimethoxybenzene	dichloromethane	N Param.: 2.48 s_N Param.: 1.09	J. Am. Chem. Soc. 2001, 123, 9500-9512 10.1021/ja010890y
allyltrimethylsilane	dichloromethane	N Param.: 1.68 s_N Param.: 1.00	J. Am. Chem. Soc. 2012, 134, 13902-13911 10.1021/ja306522b
allyltriphenylstannane	dichloromethane	N Param.: 3.09 s_N Param.: 0.90	J. Am. Chem. Soc. 2001, 123, 9500-9512 10.1021/ja010890y
(2-methylallyl)trimethylsilane	dichloromethane	N Param.: 4.41 s_N Param.: 0.96	J. Am. Chem. Soc. 2001, 123, 9500-9512 10.1021/ja010890y
allyltributylstannane	dichloromethane	N Param.: 5.46 s_N Param.: 0.89	J. Am. Chem. Soc. 2001, 123, 9500-9512 10.1021/ja010890y
(2-methylallyl)tributylstannane	dichloromethane	N Param.: 7.48 s_N Param.: 0.89	J. Am. Chem. Soc. 2001, 123, 9500-9512 10.1021/ja010890y
Danishefskys diene	dichloromethane	N Param.: 8.57 s_N Param.: 0.84	J. Am. Chem. Soc. 2001, 123, 9500-9512 10.1021/ja010890y
2-(trimethylsiloxy)-5,6-dihydro-4H-pyran	dichloromethane	N Param.: 10.61 s_N Param.: 0.86	J. Am. Chem. Soc. 2001, 123, 9500-9512 10.1021/ja010890y
5-(trimethylsiloxy)-2,3-dihydrofuran	dichloromethane	N Param.: 12.56 s_N Param.: 0.70	J. Am. Chem. Soc. 2001, 123, 9500-9512 10.1021/ja010890y
methylenecyclopentane	dichloromethane	N Param.: 2.82 s_N Param.: 0.90	J. Am. Chem. Soc. 2001, 123, 9500-9512 10.1021/ja010890y
2-methylfuran	dichloromethane	N Param.: 3.61 s_N Param.: 1.11	J. Am. Chem. Soc. 2001, 123, 9500-9512 10.1021/ja010890y
N-methylpyrrole	dichloromethane	N Param.: 5.85 s_N Param.: 1.03	J. Am. Chem. Soc. 2001, 123, 9500-9512 10.1021/ja010890y
1-(trimethylsiloxy)cyclohexene	dichloromethane	N Param.: 5.21 s_N Param.: 1.00	J. Am. Chem. Soc. 2001, 123, 9500-9512 10.1021/ja010890y
2-(trimethylsiloxy)propene	dichloromethane	N Param.: 5.41 s_N Param.: 0.91	J. Am. Chem. Soc. 2001, 123, 9500-9512 10.1021/ja010890y
1-phenyl-1-(trimethylsiloxy)ethene	dichloromethane	N Param.: 6.22 s_N Param.: 0.96	J. Am. Chem. Soc. 2001, 123, 9500-9512 10.1021/ja010890y
1-(trimethylsiloxy)cyclopentene	dichloromethane	N Param.: 6.57 s_N Param.: 0.93	J. Am. Chem. Soc. 2001, 123, 9500-9512 10.1021/ja010890y
1-phenoxy-1-(trimethylsiloxy)ethene	dichloromethane	N Param.: 8.23 s_N Param.: 0.81	J. Am. Chem. Soc. 2001, 123, 9500-9512 10.1021/ja010890y
1-(N-morpholino)cyclohexene	dichloromethane	N Param.: 11.40 s_N Param.: 0.83	J. Am. Chem. Soc. 2001, 123, 9500-9512 10.1021/ja010890y
1-(N-piperidino)cyclohexene	dichloromethane	N Param.: 13.36 s_N Param.: 0.81	J. Am. Chem. Soc. 2001, 123, 9500-9512 10.1021/ja010890y
allyltriphenylsilane	dichloromethane	N Param.: -0.13 s_N Param.: 1.21	J. Am. Chem. Soc. 2001, 123, 9500-9512 10.1021/ja010890y
methylenecyclohexane	dichloromethane	N Param.: 1.16 s_N Param.: 1.04	J. Am. Chem. Soc. 2012, 134, 13902-13911 10.1021/ja306522b
2-chloropropene	dichloromethane	N Param.: -3.65 s_N Param.: 1.97	J. Am. Chem. Soc. 2012, 134, 13902-13911 10.1021/ja306522b
1-hexene	dichloromethane	N Param.: -2.77 s_N Param.: 1.41	J. Am. Chem. Soc. 2012, 134, 13902-13911 10.1021/ja306522b
1-methylcyclohexene	dichloromethane	N Param.: 0.08 s_N Param.: 1.15	J. Am. Chem. Soc. 2001, 123, 9500-9512 10.1021/ja010890y
2-methyl-but-2-ene	dichloromethane	N Param.: 0.65 s_N Param.: 1.17	J. Am. Chem. Soc. 2001, 123, 9500-9512 10.1021/ja010890y
2-methylpropene (isobutylene)	dichloromethane	N Param.: 1.11 s_N Param.: 0.98	J. Am. Chem. Soc. 2001, 123, 9500-9512 10.1021/ja010890y
1-methyl-4-vinyl-benzene	dichloromethane	N Param.: 1.70 s_N Param.: 1.06	J. Am. Chem. Soc. 2001, 123, 9500-9512 10.1021/ja010890y
2-methyl-buta-1,3-diene (isoprene)	dichloromethane	N Param.: 1.10 s_N Param.: 0.98	J. Am. Chem. Soc. 2001, 123, 9500-9512 10.1021/ja010890y
allylchlorodimethylsilane	dichloromethane	N Param.: -0.57 s_N Param.: 1.06	J. Am. Chem. Soc. 2012, 134, 13902-13911 10.1021/ja306522b
trimethyl(prenyl)silane	dichloromethane	N Param.: 0.90 s_N Param.: 1.17	J. Am. Chem. Soc. 2001, 123, 9500-9512 10.1021/ja010890y
(2-methylallyl)triphenylgermane	dichloromethane	N Param.: 4.67 s_N Param.: 0.81	J. Am. Chem. Soc. 2001, 123, 9500-9512 10.1021/ja010890y
2,3,3-trimethyl-but-1-ene	dichloromethane	N Param.: 0.06 s_N Param.: 1.07	J. Am. Chem. Soc. 2012, 134, 13902-13911 10.1021/ja306522b
2,3-dimethyl-but-1-ene	dichloromethane	N Param.: 0.65 s_N Param.: 1.00	J. Am. Chem. Soc. 2012, 134, 13902-13911 10.1021/ja306522b
2,4,4-trimethyl-pent-1-ene	dichloromethane	N Param.: 0.79 s_N Param.: 1.07	J. Am. Chem. Soc. 2012, 134, 13902-13911 10.1021/ja306522b
furan	dichloromethane	N Param.: 1.33 s_N Param.: 1.29	J. Am. Chem. Soc. 2012, 134, 13902-13911 10.1021/ja306522b
1-methoxy-2-methyl-1-(trimethylsiloxy)propene	dichloromethane	N Param.: 9.00 s_N Param.: 0.98	J. Am. Chem. Soc. 2001, 123, 9500-9512 10.1021/ja010890y
2-methyl-1-(trimethylsiloxy)propen	dichloromethane	N Param.: 3.94 s_N Param.: 1.00	J. Am. Chem. Soc. 2001, 123, 9500-9512 10.1021/ja010890y
norbornene	dichloromethane	N Param.: -0.25 s_N Param.: 1.09	J. Am. Chem. Soc. 2012, 134, 13902-13911 10.1021/ja306522b
1-methylcyclopentene	dichloromethane	N Param.: 1.18 s_N Param.: 1.17	J. Am. Chem. Soc. 2012, 134, 13902-13911 10.1021/ja306522b