C-Nucleophiles
Name | Solvent |
Reactivity Parameters |
Classification |
Reference (title or year) |
---|---|---|---|---|
(E)-1-styryl-2-tritylpyrrolidine (in CH2Cl2)![]() ![]() |
dichloromethane | N Param.: 10.19 sN Param.: 1.06 | ![]() ![]() ![]() | J. Am. Chem. Soc. 2014, 136, 14263-14269 10.1021/ja508065e |
(E)-1-styryl-2-(triphenylsilyl)pyrrolidine (in CH2Cl2)![]() ![]() |
dichloromethane | N Param.: 11.77 sN Param.: 0.98 | ![]() ![]() ![]() | J. Am. Chem. Soc. 2014, 136, 14263-14269 10.1021/ja508065e |
Meldrum's acid iodonium ylide (in CH2Cl2)![]() ![]() |
dichloromethane | N Param.: 4.36 sN Param.: 1.06 | ![]() ![]() ![]() | J. Am. Chem. Soc. 2016, 138, 10304-10313 10.1021/jacs.6b05768 |
Dimedone iodonium ylide (in CH2Cl2)![]() ![]() |
dichloromethane | N Param.: 6.18 sN Param.: 0.81 | ![]() ![]() ![]() | J. Am. Chem. Soc. 2016, 138, 10304-10313 10.1021/jacs.6b05768 |
N,N-Dimethylbarbituric acid iodonium ylide (in CHCl2)![]() ![]() |
dichloromethane | N Param.: 7.98 sN Param.: 0.71 | ![]() ![]() ![]() | J. Am. Chem. Soc. 2016, 138, 10304-10313 10.1021/jacs.6b05768 |
6-methyl-3-(phenyl-l3-iodanylidene)dihydro-2H-pyran-2,4(3H)-dione (in CH2Cl2)![]() ![]() |
dichloromethane | N Param.: 4.67 sN Param.: 0.92 | ![]() ![]() ![]() | J. Am. Chem. Soc. 2016, 138, 10304-10313 10.1021/jacs.6b05768 |
4,4,5,5-tetramethyl-2-prop-2-enyl-1,3,2-dioxaborolane (in CH2Cl2)![]() ![]() |
dichloromethane | N Param.: -0.64 sN Param.: 1.10 | ![]() ![]() ![]() | J. Am. Chem. Soc. 2017, 139, 15324-15327 10.1021/jacs.7b10240 |
potassium allyltrifluoroborate (in MeCN)![]() ![]() |
MeCN | N Param.: 5.29 sN Param.: 0.87 | ![]() ![]() | J. Am. Chem. Soc. 2017, 139, 15324-15327 10.1021/jacs.7b10240 |
lithium 2-allyl-2-(3,5-bis(trifluoromethyl)phenyl)-4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-uide (in MeCN)![]() ![]() |
MeCN | N Param.: 8.71 sN Param.: 0.80 | ![]() ![]() ![]() | J. Am. Chem. Soc. 2017, 139, 15324-15327 10.1021/jacs.7b10240 |
lithium 2-allyl-4,4,5,5-tetramethyl-2-phenyl-1,3,2-dioxaborolan-2-uide (in MeCN)![]() ![]() |
MeCN | N Param.: 11.20 sN Param.: 0.64 | ![]() | J. Am. Chem. Soc. 2017, 139, 15324-15327 10.1021/jacs.7b10240 |
lithium (E)-2-(3,5-bis(trifluoromethyl)phenyl)-2-(but-2-en-1-yl)-4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-uide (in MeCN)![]() ![]() |
MeCN | N Param.: 9.49 sN Param.: 0.82 | ![]() ![]() ![]() | J. Am. Chem. Soc. 2017, 139, 15324-15327 10.1021/jacs.7b10240 |
(p-nitrophenyl)diazomethane![]() ![]() |
dichloromethane | N Param.: 7.17 sN Param.: 0.83 | ![]() ![]() ![]() | J. Am. Chem. Soc. 2018, 140, 16758-16772 10.1021/jacs.8b09995 |
(p-cyanophenyl)diazomethane![]() ![]() |
dichloromethane | N Param.: 7.66 sN Param.: 0.80 | ![]() ![]() ![]() | J. Am. Chem. Soc. 2018, 140, 16758-16772 10.1021/jacs.8b09995 |
(p-bromophenyl)diazomethane![]() ![]() |
dichloromethane | N Param.: 8.87 sN Param.: 0.82 | ![]() ![]() ![]() | J. Am. Chem. Soc. 2018, 140, 16758-16772 10.1021/jacs.8b09995 |
1-ethoxy-3-(4-nitrophenyl)-1,3-dioxopropan-2-ide (in DMSO)![]() ![]() |
DMSO | N Param.: 16.26 sN Param.: 0.83 | ![]() ![]() ![]() | J. Am. Chem. Soc. 2018, 140, 11474-11486 10.1021/jacs.8b07147 |
Ph3P=CH-CHO (in MeCN)![]() ![]() |
MeCN | N Param.: 9.09 sN Param.: 0.74 | ![]() ![]() ![]() | J. Am. Chem. Soc. 2016, 138, 11272-11281 10.1021/jacs.6b06264 |
Ph3P=CH-C(O)Me (in MeCN)![]() ![]() |
MeCN | N Param.: 10.27 sN Param.: 0.83 | ![]() ![]() ![]() | J. Am. Chem. Soc. 2016, 138, 11272-11281 10.1021/jacs.6b06264 |
anion of 4-(trifluoromethyl)benzyl trifluoromethyl sulfone (in MeCN)![]() ![]() |
MeCN | N Param.: 16.15 sN Param.: 0.99 | ![]() ![]() ![]() | J. Am. Chem. Soc. 2020, 142, 8383-8402 10.1021/jacs.0c01960 |
anion of 4-cyanobenzyl trifluoromethyl sulfone (in MeCN)![]() ![]() |
MeCN | N Param.: 15.62 sN Param.: 0.99 | ![]() ![]() ![]() | J. Am. Chem. Soc. 2020, 142, 8383-8402 10.1021/jacs.0c01960 |
anion of 4-nitrobenzyl-CN (in MeCN)![]() ![]() |
MeCN | N Param.: 20.10 sN Param.: 0.71 | ![]() ![]() ![]() | J. Am. Chem. Soc. 2020, 142, 8383-8402 10.1021/jacs.0c01960 |
anion of (4-NO2-C6H4)CH2SO2Ph (in MeCN)![]() ![]() |
MeCN | N Param.: 19.90 sN Param.: 0.66 | ![]() ![]() ![]() | J. Am. Chem. Soc. 2020, 142, 8383-8402 10.1021/jacs.0c01960 |
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 sN Param.: 0.57 | ![]() ![]() ![]() | J. Am. Chem. Soc. 2022, 144, 16118-16130 10.1021/jacs.2c06493 |
methyl diazoacetate![]() ![]() |
dichloromethane | N Param.: 4.68 sN Param.: 0.94 | ![]() ![]() ![]() | J. Am. Chem. Soc. 2023, 145, 7416-7434 10.1021/jacs.2c13872 |
dimethyl diazomalonate![]() ![]() |
dichloromethane | N Param.: -1.24 sN Param.: 0.81 | ![]() ![]() ![]() | J. Am. Chem. Soc. 2023, 145, 7416-7434 10.1021/jacs.2c13872 |
Indole![]() ![]() |
dichloromethane | N Param.: 5.55 sN Param.: 1.09 | ![]() ![]() ![]() | J. Org. Chem. 2006, 71, 9088-9095 10.1021/jo0614339 |
N-methylindole![]() ![]() |
dichloromethane | N Param.: 5.75 sN Param.: 1.23 | ![]() ![]() ![]() | J. Org. Chem. 2006, 71, 9088-9095 10.1021/jo0614339 |
1,2-dimethylindole![]() ![]() |
dichloromethane | N Param.: 6.54 sN Param.: 1.10 | ![]() | J. Org. Chem. 2006, 71, 9088-9095 10.1021/jo0614339 |
2-(bis(trimethylsiloxy)amino)propene![]() ![]() |
dichloromethane | N Param.: 4.76 sN Param.: 0.86 | ![]() ![]() ![]() | J. Org. Chem. 2001, 66, 3196-3200 10.1021/jo0015927 |
(bis(trimethylsiloxy)amino)styrene![]() ![]() |
dichloromethane | N Param.: 4.80 sN Param.: 0.86 | ![]() | J. Org. Chem. 2001, 66, 3196-3200 10.1021/jo0015927 |
2-(bis(tert-butyldimethylsiloxy)amino)propene![]() ![]() |
dichloromethane | N Param.: 4.23 sN Param.: 0.93 | ![]() ![]() ![]() | J. Org. Chem. 2001, 66, 3196-3200 10.1021/jo0015927 |
4-(bis(trimethylsiloxy)amino)pent-4-enoic acid methyl ester![]() ![]() |
dichloromethane | N Param.: 3.84 sN Param.: 0.87 | ![]() ![]() ![]() | J. Org. Chem. 2001, 66, 3196-3200 10.1021/jo0015927 |
anion of nitroethane (in DMSO)![]() ![]() |
DMSO | N Param.: 21.54 sN Param.: 0.62 | ![]() ![]() ![]() | J. Org. Chem. 2003, 68, 6880-6886 10.1021/jo0344182 |
anion of nitroethane (in water)![]() ![]() |
water | N Param.: 11.25 sN Param.: 0.52 | ![]() ![]() ![]() | J. Org. Chem. 2004, 69, 7565-7576 10.1021/jo048773j |
anion of nitromethane (in water)![]() ![]() |
water | N Param.: 12.06 sN Param.: 0.53 | ![]() ![]() ![]() | J. Org. Chem. 2004, 69, 7565-7576 10.1021/jo048773j |
anion of nitromethane (in DMSO)![]() ![]() |
DMSO | N Param.: 20.71 sN Param.: 0.60 | ![]() ![]() ![]() | J. Org. Chem. 2004, 69, 7565-7576 10.1021/jo048773j |
anion of 2-nitropropane (in DMSO)![]() ![]() |
DMSO | N Param.: 20.61 sN Param.: 0.69 | ![]() ![]() ![]() | J. Org. Chem. 2004, 69, 7565-7576 10.1021/jo048773j |
anion of 2-nitropropane (in water)![]() ![]() |
water | N Param.: 10.69 sN Param.: 0.56 | ![]() ![]() ![]() | J. Org. Chem. 2004, 69, 7565-7576 10.1021/jo048773j |
anion of phenylnitromethane (in H2O)![]() ![]() |
water | N Param.: 12.05 sN Param.: 0.53 | ![]() ![]() ![]() | J. Org. Chem. 2004, 69, 7565-7576 10.1021/jo048773j |
anion of phenylnitromethane (in DMSO)![]() ![]() |
DMSO | N Param.: 18.29 sN Param.: 0.71 | ![]() ![]() ![]() | J. Org. Chem. 2004, 69, 7565-7576 10.1021/jo048773j |
anion of p-tolylnitromethane (in water)![]() ![]() |
water | N Param.: 13.09 sN Param.: 0.50 | ![]() ![]() ![]() | J. Org. Chem. 2004, 69, 7565-7576 10.1021/jo048773j |
anion of p-tolylnitromethane (in DMSO)![]() ![]() |
DMSO | N Param.: 18.31 sN Param.: 0.76 | ![]() ![]() ![]() | J. Org. Chem. 2004, 69, 7565-7576 10.1021/jo048773j |
anion of (4-nitrophenyl)nitromethane (in water)![]() ![]() |
water | N Param.: 13.58 sN Param.: 0.52 | ![]() ![]() ![]() | J. Org. Chem. 2004, 69, 7565-7576 10.1021/jo048773j |
anion of (4-nitrophenyl)nitromethane (in DMSO)![]() ![]() |
DMSO | N Param.: 16.29 sN Param.: 0.75 | ![]() ![]() ![]() | J. Org. Chem. 2004, 69, 7565-7576 10.1021/jo048773j |
anion of (3-nitrophenyl)nitromethane (in water)![]() ![]() |
water | N Param.: 14.25 sN Param.: 0.46 | ![]() ![]() ![]() | J. Org. Chem. 2004, 69, 7565-7576 10.1021/jo048773j |
anion of (3-nitrophenyl)nitromethane (in DMSO)![]() ![]() |
DMSO | N Param.: 18.06 sN Param.: 0.71 | ![]() ![]() ![]() | J. Org. Chem. 2004, 69, 7565-7576 10.1021/jo048773j |
anion of (4-cyanophenyl)nitromethane (in water)![]() ![]() |
water | N Param.: 13.23 sN Param.: 0.52 | ![]() ![]() ![]() | J. Org. Chem. 2004, 69, 7565-7576 10.1021/jo048773j |
anion of (4-cyanophenyl)nitromethane (in DMSO)![]() ![]() |
DMSO | N Param.: 16.96 sN Param.: 0.73 | ![]() ![]() ![]() | J. Org. Chem. 2004, 69, 7565-7576 10.1021/jo048773j |
5-methoxy-indole![]() ![]() |
dichloromethane | N Param.: 6.22 sN Param.: 1.12 | ![]() ![]() ![]() | J. Org. Chem. 2006, 71, 9088-9095 10.1021/jo0614339 |
5-amino-indole![]() ![]() |
MeCN | N Param.: 7.22 sN Param.: 1.10 | ![]() | J. Org. Chem. 2006, 71, 9088-9095 10.1021/jo0614339 |
5-hydroxy-indole![]() ![]() |
MeCN | N Param.: 6.44 sN Param.: 1.10 | ![]() | J. Org. Chem. 2006, 71, 9088-9095 10.1021/jo0614339 |