C-Nucleophiles
Name | Solvent |
Reactivity Parameters |
Classification |
Reference (title or year) |
---|---|---|---|---|
alpha-(N-morpholino)styrene (in MeCN) | MeCN | N Param.: 10.30 sN Param.: 0.80 | Chem. Eur. J. 2018, 24, 5901-5910 10.1002/chem.201705962 | |
1-butoxy-1-(t-butyl-dimethylsiloxy)ethene | dichloromethane | N Param.: 10.32 sN Param.: 0.79 | Eur. J. Org. Chem. 2004, , 2791-2796 10.1002/ejoc.200400134 | |
1,1-bis(trimethylsiloxy)propene | dichloromethane | N Param.: 10.38 sN 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 sN Param.: 0.82 | Chem. Eur. J. 2018, 24, 5901-5910 10.1002/chem.201705962 | |
MeO-Breslow 1b | THF | N Param.: 10.45 sN Param.: 0.81 | Angew. Chem. Int. Ed. 2012, 51, 10408-10412 10.1002/anie.201204524 | |
diazomethane | dichloromethane | N Param.: 10.48 sN 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 sN 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 sN 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 sN 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 sN Param.: 0.84 | Chem. Eur. J. 2018, 24, 5901-5910 10.1002/chem.201705962 | |
2,4-dimethylpyrrole | MeCN | N Param.: 10.67 sN 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 sN Param.: 0.56 | J. Org. Chem. 2004, 69, 7565-7576 10.1021/jo048773j | |
1-(phenylmethylamino)cyclohexene | dichloromethane | N Param.: 10.73 sN Param.: 0.81 | Chem. Eur. J. 2003, 9, 2209-2218 10.1002/chem.200204666 | |
(E)-beta-(N-morpholino)styrene | dichloromethane | N Param.: 10.76 sN 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 sN 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 sN 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 sN 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 sN 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 sN Param.: 0.52 | J. Org. Chem. 2004, 69, 7565-7576 10.1021/jo048773j | |
5-(triphenylsiloxy)-2,3-dihydrofuran | dichloromethane | N Param.: 11.28 sN 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 sN Param.: 0.76 | Org. Lett. 2015, 17, 2614-2617 10.1021/acs.orglett.[...] | |
1-(N-morpholino)cyclohexene | dichloromethane | N Param.: 11.40 sN Param.: 0.83 | J. Am. Chem. Soc. 2001, 123, 9500-9512 10.1021/ja010890y | |
Desoxy Breslow intermediate 2b' | THF | N Param.: 11.42 sN Param.: 0.70 | Angew. Chem. Int. Ed. 2012, 51, 6231-6235 10.1002/anie.201202327 | |
4-methyl-5-(trimethylsiloxy)-2,3-dihydrofuran | dichloromethane | N Param.: 11.50 sN Param.: 0.91 | Eur. J. Org. Chem. 2004, , 2791-2796 10.1002/ejoc.200400134 | |
anion of 5-phenyl Meldrum's acid (in DMSO) | DMSO | N Param.: 11.54 sN Param.: 0.95 | Eur. J. Org. Chem. 2016, , 1841-1848 10.1002/ejoc.201600107 | |
alpha-(N-piperidino)styrene (in MeCN) | MeCN | N Param.: 11.60 sN Param.: 0.80 | Chem. Eur. J. 2018, 24, 5901-5910 10.1002/chem.201705962 | |
3-ethyl-2,4-dimethylpyrrole | MeCN | N Param.: 11.63 sN Param.: 0.95 | Eur. J. Org. Chem. 2008, , 2369-2374 10.1002/ejoc.200800092 | |
(E)-1-(1,2-diphenylvinyl)pyrrolidine (in MeCN) | MeCN | N Param.: 11.66 sN Param.: 0.82 | Chem. Eur. J. 2018, 24, 5901-5910 10.1002/chem.201705962 | |
(E)-4-styrylmorpholine | MeCN | N Param.: 11.66 sN Param.: 0.83 | Chem. Eur. J. 2018, 24, 5901-5910 10.1002/chem.201705962 | |
anion of dimedone (in water) | water | N Param.: 11.77 sN Param.: 0.63 | J. Am. Chem. Soc. 2003, 125, 12980-12986 10.1021/ja036838e | |
(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 | |
lithium (5-methylthiophen-2-yl)(4-(trifluoromethyl)phenyl)neopentylglycolborate | MeCN | N Param.: 11.85 sN Param.: 0.72 | Angew. Chem. Int. Ed. 2015, 54, 2780-2783 10.1002/anie.201410562 | |
(4-Br-C6H4)-(CO)-CH=SMe2 | dichloromethane | N Param.: 11.95 sN Param.: 0.76 | Angew. Chem. Int. Ed. 2009, 48, 5034-5037 10.1002/anie.200900933 | |
(E)-1-(2-(4-methoxyphenyl)-1-phenylvinyl)pyrrolidine (in MeCN) | MeCN | N Param.: 11.99 sN Param.: 0.84 | Chem. Eur. J. 2018, 24, 5901-5910 10.1002/chem.201705962 | |
2,2-dimethyl-5-(4-nitrobenzyl)-4,6-dioxo-1,3-dioxan-5-ide (in DMSO) | DMSO | N Param.: 12.02 sN Param.: 1.17 | Chem. Eur. J. 2014, 20, 11069-11077 10.1002/chem.201403161 | |
1-methyl-4-(N-morpholino)tetrahydropyridine | dichloromethane | N Param.: 12.03 sN Param.: 0.80 | Chem. Eur. J. 2003, 9, 2209-2218 10.1002/chem.200204666 | |
anion of phenylnitromethane (in H2O) | water | N Param.: 12.05 sN Param.: 0.53 | J. Org. Chem. 2004, 69, 7565-7576 10.1021/jo048773j | |
(E)-1-(N-morpholino)propene | dichloromethane | N Param.: 12.06 sN Param.: 0.80 | Chem. Eur. J. 2003, 9, 2209-2218 10.1002/chem.200204666 | |
anion of Meldrum's acid (in water) | water | N Param.: 12.06 sN Param.: 0.66 | J. Am. Chem. Soc. 2003, 125, 12980-12986 10.1021/ja036838e | |
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 2-nitropropane (in 91M9AN) | MeOH-MeCN mix | N Param.: 12.20 sN Param.: 0.71 | Eur. J. Org. Chem. 2006, , 2530-2537 10.1002/ejoc.200500769 | |
Ph3P=CH-CO2Et (in DMSO) | DMSO | N Param.: 12.21 sN Param.: 0.62 | J. Am. Chem. Soc. 2009, 131, 704-714 10.1021/ja8056216 | |
(Z)-1-(N-morpholino)propene | dichloromethane | N Param.: 12.26 sN Param.: 0.80 | Chem. Eur. J. 2003, 9, 2209-2218 10.1002/chem.200204666 | |
(E)-1-styrylpyrrolidine (in CH2Cl2) | dichloromethane | N Param.: 12.26 sN Param.: 0.93 | J. Am. Chem. Soc. 2014, 136, 14263-14269 10.1021/ja508065e | |
Ph3P=CH-CN | dichloromethane | N Param.: 12.29 sN Param.: 0.75 | J. Am. Chem. Soc. 2009, 131, 704-714 10.1021/ja8056216 | |
5-(trimethylsiloxy)-2,3-dihydrofuran (in MeCN) | MeCN | N Param.: 12.34 sN Param.: 0.72 | J. Am. Chem. Soc. 2013, 135, 6579-6587 10.1021/ja401106x | |
anion of 5-(p-anisyl) Meldrum's acid (in DMSO) | DMSO | N Param.: 12.35 sN Param.: 0.90 | Eur. J. Org. Chem. 2016, , 1841-1848 10.1002/ejoc.201600107 | |
1-(1-cyclohexenyl)-4-methylpiperazine | dichloromethane | N Param.: 12.51 sN Param.: 0.80 | Chem. Eur. J. 2003, 9, 2209-2218 10.1002/chem.200204666 | |
anion of phenylnitromethane (in 91M9AN) | MeOH-MeCN mix | N Param.: 12.51 sN Param.: 0.67 | Eur. J. Org. Chem. 2006, , 2530-2537 10.1002/ejoc.200500769 | |
(5-methyl-furan-2-yl)(1,1,1-tris(methoxy)ethane)borate | MeCN | N Param.: 12.55 sN Param.: 0.92 | Chem. Sci. 2012, 3, 878-882 10.1039/c2sc00883a | |
5-(trimethylsiloxy)-2,3-dihydrofuran | dichloromethane | N Param.: 12.56 sN Param.: 0.70 | J. Am. Chem. Soc. 2001, 123, 9500-9512 10.1021/ja010890y | |
Desoxy Breslow intermediate 2c' | THF | N Param.: 12.75 sN Param.: 0.71 | Angew. Chem. Int. Ed. 2012, 51, 6231-6235 10.1002/anie.201202327 | |
Ph3P=CH-CO2Et | dichloromethane | N Param.: 12.79 sN Param.: 0.77 | J. Am. Chem. Soc. 2009, 131, 704-714 10.1021/ja8056216 | |
1-(phenylmethylamino)cyclopentene | dichloromethane | N Param.: 12.90 sN Param.: 0.79 | Chem. Eur. J. 2003, 9, 2209-2218 10.1002/chem.200204666 | |
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 | |
Ph3P=C(CH3)-CO2Et | dichloromethane | N Param.: 13.09 sN Param.: 0.73 | J. Am. Chem. Soc. 2009, 131, 704-714 10.1021/ja8056216 | |
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 | |
1-(N-piperidino)cyclohexene | dichloromethane | N Param.: 13.36 sN Param.: 0.81 | J. Am. Chem. Soc. 2001, 123, 9500-9512 10.1021/ja010890y | |
1-(N-morpholino)cyclopentene | dichloromethane | N Param.: 13.41 sN Param.: 0.82 | Chem. Eur. J. 2003, 9, 2209-2218 10.1002/chem.200204666 | |
anion of nitroethane (in 91M9AN) | MeOH-MeCN mix | N Param.: 13.41 sN Param.: 0.67 | Eur. J. Org. Chem. 2006, , 2530-2537 10.1002/ejoc.200500769 | |
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 p-tolylnitromethane (in 91M9AN) | MeOH-MeCN mix | N Param.: 13.58 sN Param.: 0.64 | Eur. J. Org. Chem. 2006, , 2530-2537 10.1002/ejoc.200500769 | |
anion of diethyl 2-(benzoyl)malonate (in DMSO) | DMSO | N Param.: 13.63 sN Param.: 0.80 | Eur. J. Org. Chem. 2016, , 1841-1848 10.1002/ejoc.201600107 | |
anion of acetylacetone (in water) | water | N Param.: 13.73 sN Param.: 0.64 | J. Am. Chem. Soc. 2003, 125, 12980-12986 10.1021/ja036838e | |
(4-Br-C6H4)-(CO)-CH=SMe2 (in DMSO) | DMSO | N Param.: 13.78 sN Param.: 0.72 | J. Am. Chem. Soc. 2010, 132, 17894-17900 10.1021/ja1084749 | |
5-(4-cyanobenzyl)-2,2-dimethyl-4,6-dioxo-1,3-dioxan-5-ide (in DMSO) | DMSO | N Param.: 13.79 sN Param.: 0.86 | Chem. Eur. J. 2014, 20, 11069-11077 10.1002/chem.201403161 | |
anion of diethyl 2-(acetyl)malonate (in DMSO) | DMSO | N Param.: 13.83 sN Param.: 0.84 | Eur. J. Org. Chem. 2016, , 1841-1848 10.1002/ejoc.201600107 | |
(E)-beta-(N-piperidino)styrene (in MeCN) | MeCN | N Param.: 13.84 sN Param.: 0.73 | Chem. Eur. J. 2018, 24, 5901-5910 10.1002/chem.201705962 | |
(E)-1-styrylpyrrolidine (in MeCN) | MeCN | N Param.: 13.87 sN Param.: 0.76 | Chem. Eur. J. 2018, 24, 5901-5910 10.1002/chem.201705962 | |
anion of Meldrums acid (in DMSO) | DMSO | N Param.: 13.91 sN Param.: 0.86 | Angew. Chem. Int. Ed. 2002, 41, 91-95 10.1002/1521-3773(20[...] | |
Desoxy Breslow intermediate 2b | THF | N Param.: 13.91 sN Param.: 0.64 | Angew. Chem. Int. Ed. 2012, 51, 6231-6235 10.1002/anie.201202327 | |
anion of 2-nitro-1-phenylethan-1-one (in DMSO) | DMSO | N Param.: 13.91 sN Param.: 0.76 | Chem. Eur. J. 2015, 21, 875-884 10.1002/chem.201404500 | |
anion of (4-cyanophenyl)nitromethane (in 91M9AN) | MeOH-MeCN mix | N Param.: 13.92 sN Param.: 0.74 | Eur. J. Org. Chem. 2006, , 2530-2537 10.1002/ejoc.200500769 | |
(C6H5)-(CO)-CH=SMe2 (in DMSO) | DMSO | N Param.: 13.95 sN Param.: 0.69 | J. Am. Chem. Soc. 2010, 132, 17894-17900 10.1021/ja1084749 | |
anion of nitromethane (in 91M9AN) | MeOH-MeCN mix | N Param.: 14.02 sN Param.: 0.61 | Eur. J. Org. Chem. 2006, , 2530-2537 10.1002/ejoc.200500769 | |
1-(N-piperidino)cyclohexene (in MeCN) | MeCN | N Param.: 14.02 sN Param.: 0.76 | J. Am. Chem. Soc. 2013, 135, 6579-6587 10.1021/ja401106x | |
anion of (4-nitrophenyl)nitromethane (in 91M9AN) | MeOH-MeCN mix | N Param.: 14.05 sN Param.: 0.72 | Eur. J. Org. Chem. 2006, , 2530-2537 10.1002/ejoc.200500769 | |
1,3,4-triphenyl-1H-1,2,4-triazol-4-ium-5-ide (in THF) | THF | N Param.: 14.07 sN Param.: 0.84 | Angew. Chem. Int. Ed. 2011, 50, 6915-6919 10.1002/anie.201102435 | |
1-pyrrolidino-3,4-dihydronaphthalene (in MeCN) | MeCN | N Param.: 14.09 sN Param.: 0.66 | Synthesis 2019, 51, 1157-1170 10.1055/s-0037-1611634 | |
2-thiobarbiturate anion (in DMSO) | DMSO | N Param.: 14.24 sN Param.: 0.82 | J. Org. Chem. 2017, 82, 8476-8488 10.1021/acs.joc.7b01223 | |
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-methyl acetylacetone (in water) | water | N Param.: 14.33 sN Param.: 0.69 | J. Am. Chem. Soc. 2003, 125, 12980-12986 10.1021/ja036838e | |
(Z)-1-(1,3-dimesityl-1H-imidazol-3-ium-2-yl)-2-phenylprop-1-en-1-olate (in DMSO) | DMSO | N Param.: 14.40 sN Param.: 0.64 | Angew. Chem. Int. Ed. 2013, 52, 11163-11167 10.1002/ange.201303524 | |
(Z)-2-phenyl-1-(1,3,4-triphenyl-4H-1,2,4-triazol-1-ium-5-yl)prop-1-en-1-olate (in THF) | THF | N Param.: 14.40 sN Param.: 0.66 | Angew. Chem. Int. Ed. 2013, 52, 11163-11167 10.1002/ange.201303524 | |
Desoxy Breslow intermediate 2a' | THF | N Param.: 14.45 sN Param.: 0.71 | Angew. Chem. Int. Ed. 2012, 51, 6231-6235 10.1002/anie.201202327 | |
3-methyl-2,4-dioxotetrahydro-2H-pyran-3-ide (in DMSO) | DMSO | N Param.: 14.46 sN Param.: 0.91 | Eur. J. Org. Chem. 2015, , 7594-7601 10.1002/ejoc.201501107 | |
(4-MeO-C6H4)-(CO)-CH=SMe2 (in DMSO) | DMSO | N Param.: 14.48 sN Param.: 0.71 | J. Am. Chem. Soc. 2010, 132, 17894-17900 10.1021/ja1084749 | |
5-(4-(dimethylamino)benzyl)-2,2-dimethyl-4,6-dioxo-1,3-dioxan-5-ide (in DMSO) | DMSO | N Param.: 14.48 sN Param.: 0.86 | Chem. Eur. J. 2014, 20, 11069-11077 10.1002/chem.201403161 | |
anion of 4-nitrobenzyl trifluoromethyl sulfone (in DMSO) | DMSO | N Param.: 14.49 sN Param.: 0.86 | J. Am. Chem. Soc. 2007, 129, 9753-9761 10.1021/ja072135b | |
anion of (3-nitrophenyl)nitromethane (in 91M9AN) | MeOH-MeCN mix | N Param.: 14.75 sN Param.: 0.71 | Eur. J. Org. Chem. 2006, , 2530-2537 10.1002/ejoc.200500769 | |
MeO-Breslow 1a | THF | N Param.: 14.77 sN Param.: 0.80 | Angew. Chem. Int. Ed. 2012, 51, 10408-10412 10.1002/anie.201204524 | |
1,3-diethyl-thiobarbiturate anion (in DMSO) | DMSO | N Param.: 14.90 sN Param.: 0.80 | J. Org. Chem. 2017, 82, 8476-8488 10.1021/acs.joc.7b01223 | |
1-(N-pyrrolidino)cyclohexene | dichloromethane | N Param.: 14.91 sN Param.: 0.86 | Chem. Eur. J. 2003, 9, 2209-2218 10.1002/chem.200204666 | |
anion of diethyl 2-(4-nitrophenyl)malonate (in DMSO) | DMSO | N Param.: 14.94 sN Param.: 0.96 | Eur. J. Org. Chem. 2016, , 1841-1848 10.1002/ejoc.201600107 | |
methyl (cyclohexen-1-yl)prolinate (in MeCN) | MeCN | N Param.: 14.96 sN Param.: 0.68 | Angew. Chem. Int. Ed. 2010, 49, 9526-9529 10.1002/anie.201004344 | |
anion of 1,2,3-triphenylpropane-1,3-dione (in DMSO) | DMSO | N Param.: 14.99 sN Param.: 0.83 | Eur. J. Org. Chem. 2017, , 1196-1202 10.1002/ejoc.201601513 | |
5-benzyl-2,2-dimethyl-4,6-dioxo-1,3-dioxan-5-ide (in DMSO) | DMSO | N Param.: 15.02 sN Param.: 0.75 | Chem. Eur. J. 2014, 20, 11069-11077 10.1002/chem.201403161 | |
1-(N-piperidino)cyclopentene | dichloromethane | N Param.: 15.06 sN Param.: 0.82 | Chem. Eur. J. 2003, 9, 2209-2218 10.1002/chem.200204666 | |
anion of (phenylmethylenedisulfonyl)dibenzene (in DMSO) | DMSO | N Param.: 15.07 sN Param.: 0.79 | Eur. J. Org. Chem. 2017, , 1196-1202 10.1002/ejoc.201601513 | |
5-(4-(methoxy)benzyl)-2,2-dimethyl-4,6-dioxo-1,3-dioxan-5-ide (in DMSO) | DMSO | N Param.: 15.13 sN Param.: 0.75 | Chem. Eur. J. 2014, 20, 11069-11077 10.1002/chem.201403161 |