Nucleophiles

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Name	Solvent	Reactivity Parameters	Reference (title or year)
1,2,4,5-tetramethylcyclohexa-1,4-diene (in CH2Cl2)	dichloromethane	N Param.: 4.27 s_N Param.: 0.86	J. Am. Chem. Soc. 2014, 136, 13863-13873 10.1021/ja507598y
2-(bis(tert-butyldimethylsiloxy)amino)propene	dichloromethane	N Param.: 4.23 s_N Param.: 0.93	J. Org. Chem. 2001, 66, 3196-3200 10.1021/jo0015927
isobutylenyl-ethylether	dichloromethane	N Param.: 4.23 s_N Param.: 1.00	Acc. Chem. Res. 2003, 36, 66-77 10.1021/ar020094c
(4-methoxyphenyl)dimethylsilane	dichloromethane	N Param.: 4.23 s_N Param.: 0.73	Chem. Eur. J. 2013, 19, 249-263 10.1002/chem.201202839
(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
(2-methylallyl)triphenylsilane	dichloromethane	N Param.: 4.17 s_N Param.: 0.79	J. Am. Chem. Soc. 2001, 123, 9500-9512 10.1021/ja010890y
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
potassium (1-(tert-butoxycarbonyl)-1H-indol-3-yl)trifluoroborate	MeCN	N Param.: 4.06 s_N Param.: 0.79	J. Am. Chem. Soc. 2013, 135, 6317-6324 10.1021/ja4017655
(tris(trimethylsilyl)siloxy)ethene	dichloromethane	N Param.: 4.01 s_N Param.: 0.83	Org. Lett. 2010, 12, 5206-5209 10.1021/ol102220e
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
triethylgermane	dichloromethane	N Param.: 4.00 s_N Param.: 0.75	Chem. Eur. J. 2013, 19, 249-263 10.1002/chem.201202839
10-methyl-9,10-dihydroacridine (in MeCN)	MeCN	N Param.: 4.00 s_N Param.: 0.70	Chem. Eur. J. 2013, 19, 249-263 10.1002/chem.201202839
triphenylgermane	dichloromethane	N Param.: 3.99 s_N Param.: 0.62	J. Am. Chem. Soc. 2001, 123, 9500-9512 10.1021/ja010890y
tributylsilane	dichloromethane	N Param.: 3.99 s_N Param.: 0.73	Chem. Eur. J. 2013, 19, 249-263 10.1002/chem.201202839
1H-indole-5-carboxylic acid	MeCN	N Param.: 3.97 s_N Param.: 1.10	J. Org. Chem. 2006, 71, 9088-9095 10.1021/jo0614339
diazoacetone	dichloromethane	N Param.: 3.96 s_N Param.: 0.91	Chem. Eur. J. 2003, 9, 4068-4076 10.1002/chem.200304913
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
6,6-dimethylfulvene	MeCN	N Param.: 3.93 s_N Param.: 0.88	Eur. J. Org. Chem. 2009, , 1202-1206 10.1002/ejoc.200801099
ethyl-vinylether	dichloromethane	N Param.: 3.92 s_N Param.: 0.90	Acc. Chem. Res. 2003, 36, 66-77 10.1021/ar020094c
trihexylsilane	dichloromethane	N Param.: 3.89 s_N Param.: 0.73	Chem. Eur. J. 2013, 19, 249-263 10.1002/chem.201202839