C-Nucleophiles

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Name	Solvent	Reactivity Parameters	Reference (title or year)
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
(E)-1-(2-(4-nitrophenyl)-1-phenylvinyl)pyrrolidine (in MeCN)	MeCN	N Param.: 10.42 s_N Param.: 0.82	Chem. Eur. J. 2018, 24, 5901-5910 10.1002/chem.201705962
MeO-Breslow 1b	THF	N Param.: 10.45 s_N Param.: 0.81	Angew. Chem. Int. Ed. 2012, 51, 10408-10412 10.1002/anie.201204524
diazomethane	dichloromethane	N Param.: 10.48 s_N Param.: 0.78	Chem. Eur. J. 2003, 9, 4068-4076 10.1002/chem.200304913
2-(trimethylsiloxy)-5,6-dihydro-4H-pyran (in MeCN)	MeCN	N Param.: 10.52 s_N Param.: 0.78	J. Am. Chem. Soc. 2013, 135, 6579-6587 10.1021/ja401106x
(S,E)-2-(diphenyl(trimethylsiloxy)methyl)-1-styrylpyrrolidine	MeCN	N Param.: 10.56 s_N Param.: 1.01	Angew. Chem. Int. Ed. 2012, 51, 5739-5742 10.1002/anie.201201240
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
(E)-4-(2-phenyl-2-(pyrrolidin-1-yl)vinyl)benzonitrile (in MeCN)	MeCN	N Param.: 10.63 s_N Param.: 0.84	Chem. Eur. J. 2018, 24, 5901-5910 10.1002/chem.201705962
2,4-dimethylpyrrole	MeCN	N Param.: 10.67 s_N Param.: 0.91	Eur. J. Org. Chem. 2008, , 2369-2374 10.1002/ejoc.200800092
anion of 2-nitropropane (in water)	water	N Param.: 10.69 s_N Param.: 0.56	J. Org. Chem. 2004, 69, 7565-7576 10.1021/jo048773j
1-(phenylmethylamino)cyclohexene	dichloromethane	N Param.: 10.73 s_N Param.: 0.81	Chem. Eur. J. 2003, 9, 2209-2218 10.1002/chem.200204666
(E)-beta-(N-morpholino)styrene	dichloromethane	N Param.: 10.76 s_N Param.: 0.87	Chem. Eur. J. 2003, 9, 2209-2218 10.1002/chem.200204666
lithium 4,4,5,5-tetramethyl-2-phenyl-2-(1-phenylethyl)-1,3,2-dioxaborolan-2-uide (in MeCN)	MeCN	N Param.: 10.97 s_N Param.: 0.63	Org. Lett. 2015, 17, 2614-2617 10.1021/acs.orglett.[...]
lithium 4,4,5,5-tetramethyl-2-phenyl-2-(prop-1-en-2-yl)-1,3,2-dioxaborolan-2-uide (in MeCN)	MeCN	N Param.: 11.00 s_N Param.: 0.57	J. Am. Chem. Soc. 2022, 144, 16118-16130 10.1021/jacs.2c06493
lithium 2-allyl-4,4,5,5-tetramethyl-2-phenyl-1,3,2-dioxaborolan-2-uide (in MeCN)	MeCN	N Param.: 11.20 s_N Param.: 0.64	J. Am. Chem. Soc. 2017, 139, 15324-15327 10.1021/jacs.7b10240
lithium (5-methylthiophen-2-yl)(3,5-bis(trifluoromethyl)phenyl)glycolborate	MeCN	N Param.: 11.23 s_N Param.: 0.77	Angew. Chem. Int. Ed. 2015, 54, 2780-2783 10.1002/anie.201410562
anion of nitroethane (in water)	water	N Param.: 11.25 s_N Param.: 0.52	J. Org. Chem. 2004, 69, 7565-7576 10.1021/jo048773j
5-(triphenylsiloxy)-2,3-dihydrofuran	dichloromethane	N Param.: 11.28 s_N Param.: 0.91	Eur. J. Org. Chem. 2005, , 1760-1764 10.1002/ejoc.200400706
lithium 5,5-dimethyl-2-(1-phenylethyl)-2-(4-(trifluoromethyl)phenyl)-1,3,2-dioxaborinan-2-uide (in MeCN)	MeCN	N Param.: 11.29 s_N Param.: 0.76	Org. Lett. 2015, 17, 2614-2617 10.1021/acs.orglett.[...]
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