Nucleophiles

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Name	Solvent	Reactivity Parameters	Reference (title or year)
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
bis(4-nitrophenyl)methanide (in DMSO)	DMSO	N Param.: 19.92 s_N Param.: 0.67	ARKIVOC 2008, (x), 37-53 10.3998/ark.5550190.[...]
(F)2-HBTM (in CH2Cl2)	dichloromethane	N Param.: 10.83 s_N Param.: 0.80	ARKIVOC 2024, (4), 202312093 10.24820/ark.5550190[...]
methanol (in MeCN)	MeCN	N Param.: 6.86 s_N Param.: 0.73	Bull. Chem. Soc. Jpn. 2018, 91, 523-530 10.1246/bcsj.20170360
ethanol (in MeCN)	MeCN	N Param.: 7.13 s_N Param.: 0.71	Bull. Chem. Soc. Jpn. 2018, 91, 523-530 10.1246/bcsj.20170360
isopropanol (in MeCN)	MeCN	N Param.: 6.82 s_N Param.: 0.70	Bull. Chem. Soc. Jpn. 2018, 91, 523-530 10.1246/bcsj.20170360
tert-butanol (in MeCN)	MeCN	N Param.: 5.35 s_N Param.: 0.72	Bull. Chem. Soc. Jpn. 2018, 91, 523-530 10.1246/bcsj.20170360
water (in MeCN)	MeCN	N Param.: 5.79 s_N Param.: 0.72	Bull. Chem. Soc. Jpn. 2018, 91, 523-530 10.1246/bcsj.20170360
91% n-propanol/9% MeCN (v/v)	nPrOH-MeCN mix	N Param.: 7.05 s_N Param.: 0.80	Can. J. Chem. 2005, 83, 1554-1560 10.1139%2Fv05-170
91% propan-2-ol/9% MeCN (v/v)	iPrOH-MeCN mix	N Param.: 6.49 s_N Param.: 0.96	Can. J. Chem. 2005, 83, 1554-1560 10.1139%2Fv05-170
methanolate (in methanol)	MeOH	N Param.: 15.78 s_N Param.: 0.56	Can. J. Chem. 2005, 83, 1554-1560 10.1139%2Fv05-170
ethanolate (in ethanol)	EtOH	N Param.: 15.78 s_N Param.: 0.65	Can. J. Chem. 2005, 83, 1554-1560 10.1139%2Fv05-170
n-propanolate (in propan-1-ol)	nPrOH	N Param.: 16.03 s_N Param.: 0.70	Can. J. Chem. 2005, 83, 1554-1560 10.1139%2Fv05-170
isopropanolate (in propan-2-ol)	iPrOH	N Param.: 17.03 s_N Param.: 0.63	Can. J. Chem. 2005, 83, 1554-1560 10.1139%2Fv05-170
methanolate (in 91M9AN)	MeOH-MeCN mix	N Param.: 14.51 s_N Param.: 0.68	Can. J. Chem. 2005, 83, 1554-1560 10.1139%2Fv05-170
ethanolate (in 91E9AN)	EtOH-MeCN mix	N Param.: 16.08 s_N Param.: 0.62	Can. J. Chem. 2005, 83, 1554-1560 10.1139%2Fv05-170
n-propanolate (in 91nPr9AN)	nPrOH-MeCN mix	N Param.: 16.73 s_N Param.: 0.63	Can. J. Chem. 2005, 83, 1554-1560 10.1139%2Fv05-170
isopropanolate (in 91iPr9AN)	iPrOH-MeCN mix	N Param.: 17.71 s_N Param.: 0.58	Can. J. Chem. 2005, 83, 1554-1560 10.1139%2Fv05-170
2-phenyl-1,3-dimethyl-benzimidazoline	MeCN	N Param.: 9.72 s_N Param.: 0.72	Chem. Asian J. 2009, 4, 1824-1829 10.1002/asia.200900322
2-(p-anisyl)-1,3-dimethyl-benzimidazoline	MeCN	N Param.: 10.01 s_N Param.: 0.72	Chem. Asian J. 2009, 4, 1824-1829 10.1002/asia.200900322
2-(p-tolyl)-1,3-dimethyl-benzimidazoline	MeCN	N Param.: 10.14 s_N Param.: 0.70	Chem. Asian J. 2009, 4, 1824-1829 10.1002/asia.200900322
1-(trimethylsiloxy)cyclopentene (in MeCN)	MeCN	N Param.: 6.43 s_N Param.: 0.89	Chem. Asian J. 2012, 7, 1401-1407 10.1002/asia.201101046
DBU (in MeCN)	MeCN	N Param.: 15.29 s_N Param.: 0.70	Chem. Commun. 2008, , 1792-1794 10.1039/b801811a
DBN (in MeCN)	MeCN	N Param.: 16.28 s_N Param.: 0.67	Chem. Commun. 2008, , 1792-1794 10.1039/b801811a
2-((2,2,5,5-tetramethyl-1-(prop-1-en-1-yl)-2,5-dihydro-1H-imidazol-4-yl)thio)acetonitrile (in MeCN)	MeCN	N Param.: 9.25 s_N Param.: 0.84	Chem. Commun. 2023, 59, 8091-8084 10.1039/d3cc01912h
2-((2,2,5,5-tetramethyl-1-styryl-2,5-dihydro-1H-imidazol-4-yl)thio)acetonitrile (in MeCN)	MeCN	N Param.: 7.74 s_N Param.: 0.87	Chem. Commun. 2023, 59, 8091-8084 10.1039/d3cc01912h
2-((2,2,5,5-tetramethyl-1-styryl-2,5-dihydro-1H-imidazol-4-yl)thio)acetonitrile (in CH2Cl2)	dichloromethane	N Param.: 7.06 s_N Param.: 1.11	Chem. Commun. 2023, 59, 8091-8084 10.1039/d3cc01912h
(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-(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
phenylsilane	dichloromethane	N Param.: 0.06 s_N Param.: 0.71	Chem. Eur. J. 2013, 19, 249-263 10.1002/chem.201202839
triphenylsilane	dichloromethane	N Param.: 2.65 s_N Param.: 0.72	Chem. Eur. J. 2013, 19, 249-263 10.1002/chem.201202839
dimethyl(phenyl)silane	dichloromethane	N Param.: 3.55 s_N Param.: 0.75	Chem. Eur. J. 2013, 19, 249-263 10.1002/chem.201202839
tributylsilane	dichloromethane	N Param.: 3.99 s_N Param.: 0.73	Chem. Eur. J. 2013, 19, 249-263 10.1002/chem.201202839
1-(N-pyrrolidino)cyclopentene	dichloromethane	N Param.: 15.91 s_N Param.: 0.86	Chem. Eur. J. 2003, 9, 2209-2218 10.1002/chem.200204666
1-(N-piperidino)cyclopentene	dichloromethane	N Param.: 15.06 s_N Param.: 0.82	Chem. Eur. J. 2003, 9, 2209-2218 10.1002/chem.200204666
1-(N-pyrrolidino)cyclohexene	dichloromethane	N Param.: 14.91 s_N Param.: 0.86	Chem. Eur. J. 2003, 9, 2209-2218 10.1002/chem.200204666
1-(N-morpholino)cyclopentene	dichloromethane	N Param.: 13.41 s_N Param.: 0.82	Chem. Eur. J. 2003, 9, 2209-2218 10.1002/chem.200204666
1-(phenylmethylamino)cyclopentene	dichloromethane	N Param.: 12.90 s_N Param.: 0.79	Chem. Eur. J. 2003, 9, 2209-2218 10.1002/chem.200204666
1-(phenylmethylamino)cyclohexene	dichloromethane	N Param.: 10.73 s_N Param.: 0.81	Chem. Eur. J. 2003, 9, 2209-2218 10.1002/chem.200204666