Nucleophiles

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Name	Solvent	Reactivity Parameters	Reference (title or year)
2-(trimethylsiloxy)propene	dichloromethane	N Param.: 5.41 s_N Param.: 0.91	J. Am. Chem. Soc. 2001, 123, 9500-9512 10.1021/ja010890y
4-methoxy-indole	MeCN	N Param.: 5.41 s_N Param.: 1.10	J. Org. Chem. 2006, 71, 9088-9095 10.1021/jo0614339
3-methyl-2-(trimethylsiloxy)but-1-ene	dichloromethane	N Param.: 5.41 s_N Param.: 0.90	Acc. Chem. Res. 2003, 36, 66-77 10.1021/ar020094c
2-(1-azidovinyl)naphthalene	dichloromethane	N Param.: 5.39 s_N Param.: 0.89	Chem. Commun. 2026, 62, 5041-5045 10.1039/d6cc00190d
2-(triisopropylsiloxy)propene	dichloromethane	N Param.: 5.38 s_N Param.: 0.85	J. Am. Chem. Soc. 2001, 123, 9500-9512 10.1021/ja010890y
90% water/10%EtOH (v/v)	water-EtOH mix	N Param.: 5.38 s_N Param.: 0.91	J. Am. Chem. Soc. 2004, 126, 5174-5181 10.1021/ja031828z
2-phenyl-allyltrimethylsilane	dichloromethane	N Param.: 5.38 s_N Param.: 0.89	Chem. Eur. J. 2014, 20, 1103-1110 10.1002/chem.201303215
dimethyl((trimethylgermyl)methyl)silane	dichloromethane	N Param.: 5.36 s_N Param.: 0.62	Chem. Eur. J. 2013, 19, 249-263 10.1002/chem.201202839
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
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
diphenyldiazomethane	dichloromethane	N Param.: 5.29 s_N Param.: 0.92	Chem. Eur. J. 2003, 9, 4068-4076 10.1002/chem.200304913
potassium allyltrifluoroborate (in MeCN)	MeCN	N Param.: 5.29 s_N Param.: 0.87	J. Am. Chem. Soc. 2017, 139, 15324-15327 10.1021/jacs.7b10240
1-(trimethylsiloxy)cyclohexene	dichloromethane	N Param.: 5.21 s_N Param.: 1.00	J. Am. Chem. Soc. 2001, 123, 9500-9512 10.1021/ja010890y
H2O (in water)	water	N Param.: 5.20 s_N Param.: 0.89	J. Am. Chem. Soc. 2004, 126, 5174-5181 10.1021/ja031828z
HOs(CO)2Cp*	dichloromethane	N Param.: 5.20 s_N Param.: 0.95	Chem. Eur. J. 2013, 19, 249-263 10.1002/chem.201202839
Dimethyl 1,1'-isopropylidenezirconocene	dichloromethane	N Param.: 5.20 s_N Param.: 1.00	Chem. Eur. J. 2016, 22, 11196-11200 10.1002/chem.201602452
10% ethanol/90% MeCN (v/v)	EtOH-MeCN mix	N Param.: 5.19 s_N Param.: 0.96	J. Am. Chem. Soc. 2004, 126, 5174-5181 10.1021/ja031828z
(Z)-1-phenyl-1-(trimethylsiloxy)propene (in MeCN)	MeCN	N Param.: 5.18 s_N Param.: 0.94	Synthesis 2019, 51, 1157-1170 10.1055/s-0037-1611634
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
91% water/9% MeCN (v/v)	water-MeCN mix	N Param.: 5.16 s_N Param.: 0.91	J. Am. Chem. Soc. 2004, 126, 5174-5181 10.1021/ja031828z