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 |