Enamines, Enamides, and Ynamides
| Name | Solvent |
Reactivity Parameters |
Classification |
Reference (title or year) |
|---|---|---|---|---|
(cyclohexen-1-yl)prolinate (in MeCN)  |
MeCN | N Param.: 18.86 sN Param.: 0.70 |  | Angew. Chem. Int. Ed. 2010, 49, 9526-9529 10.1002/anie.201004344 |
1-(N-pyrrolidino)cyclohexene (in MeCN) |
MeCN | N Param.: 16.42 sN Param.: 0.70 | | Angew. Chem. Int. Ed. 2010, 49, 9526-9529 10.1002/anie.201004344 |
1-(N-pyrrolidino)cyclopentene |
dichloromethane | N Param.: 15.91 sN Param.: 0.86 | | Chem. Eur. J. 2003, 9, 2209-2218 10.1002/chem.200204666 |
3-pyrrolidino-1H-indene (in MeCN) |
MeCN | N Param.: 15.27 sN Param.: 0.93 | | Synthesis 2019, 51, 1157-1170 10.1055/s-0037-1611634 |
1-(N-piperidino)cyclopentene |
dichloromethane | N Param.: 15.06 sN Param.: 0.82 | | Chem. Eur. J. 2003, 9, 2209-2218 10.1002/chem.200204666 |
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 |
1-(N-pyrrolidino)cyclohexene |
dichloromethane | N Param.: 14.91 sN Param.: 0.86 | | Chem. Eur. J. 2003, 9, 2209-2218 10.1002/chem.200204666 |
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 |
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 |
(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 |
(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 |
1-(N-morpholino)cyclopentene |
dichloromethane | N Param.: 13.41 sN Param.: 0.82 | | Chem. Eur. J. 2003, 9, 2209-2218 10.1002/chem.200204666 |
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-(phenylmethylamino)cyclopentene |
dichloromethane | N Param.: 12.90 sN Param.: 0.79 | | Chem. Eur. J. 2003, 9, 2209-2218 10.1002/chem.200204666 |
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 |
(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 |
(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 |
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 |
(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 |
(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 |
(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 |
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 |
1-(N-morpholino)cyclohexene |
dichloromethane | N Param.: 11.40 sN Param.: 0.83 | | J. Am. Chem. Soc. 2001, 123, 9500-9512 10.1021/ja010890y |
(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 |
1-(phenylmethylamino)cyclohexene |
dichloromethane | N Param.: 10.73 sN Param.: 0.81 | | Chem. Eur. J. 2003, 9, 2209-2218 10.1002/chem.200204666 |
(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 |
(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 |
(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 |
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 |
(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 |
morpholinoisobutylene |
dichloromethane | N Param.: 10.04 sN Param.: 0.82 | | Chem. Eur. J. 2003, 9, 2209-2218 10.1002/chem.200204666 |
alpha-(N-morpholino)styrene |
dichloromethane | N Param.: 9.96 sN Param.: 0.79 | | Chem. Eur. J. 2003, 9, 2209-2218 10.1002/chem.200204666 |
(E)-1-(1,2-diphenylvinyl)piperidine (in MeCN) |
MeCN | N Param.: 9.94 sN Param.: 0.86 | | Chem. Eur. J. 2018, 24, 5901-5910 10.1002/chem.201705962 |
(E)-4-(ethylthio)-2,2,5,5-tetramethyl-1-(3-phenylprop-1-en-1-yl)-2,5-dihydro-1H-imidazole (in MeCN) |
MeCN | N Param.: 9.64 sN Param.: 0.70 | | Chem. Eur. J. 2023, , EarlyView 10.1002/chem.202302764 |
ethyl (E)-3-(dimethylamino)acrylate |
dichloromethane | N Param.: 9.43 sN Param.: 0.80 | | Chem. Eur. J. 2003, 9, 2209-2218 10.1002/chem.200204666 |
2-((2,2,5,5-tetramethyl-1-(prop-1-en-1-yl)-2,5-dihydro-1H-imidazol-4-yl)thio)acetonitrile (in MeCN) |
MeCN | N Param.: 9.25 sN Param.: 0.84 | | Chem. Commun. 2023, 59, 8091-8084 10.1039/d3cc01912h |
(E)-2-((1-(but-1-en-1-yl)-2,2,5,5-tetramethyl-2,5-dihydro-1H-imidazol-4-yl)thio)acetonitrile (in MeCN) |
MeCN | N Param.: 9.23 sN Param.: 0.74 | | Chem. Eur. J. 2023, , EarlyView 10.1002/chem.202302764 |
(E)-4-(1,2-diphenylvinyl)morpholine (in MeCN) |
MeCN | N Param.: 8.78 sN Param.: 0.83 | | Chem. Eur. J. 2018, 24, 5901-5910 10.1002/chem.201705962 |
ethyl (E)-3-(N-morpholino)acrylate |
dichloromethane | N Param.: 8.52 sN Param.: 0.80 | | Chem. Eur. J. 2003, 9, 2209-2218 10.1002/chem.200204666 |
(E)-4-(benzylthio)-2,2,5,5-tetramethyl-1-styryl-2,5-dihydro-1H-imidazole (in MeCN) |
MeCN | N Param.: 8.30 sN Param.: 0.84 | | Chem. Eur. J. 2023, , EarlyView 10.1002/chem.202302764 |
(E)-4-(ethylthio)-2,2,5,5-tetramethyl-1-styryl-2,5-dihydro-1H-imidazole (in CH2Cl2) |
dichloromethane | N Param.: 8.13 sN Param.: 0.97 | | Chem. Eur. J. 2023, , EarlyView 10.1002/chem.202302764 |
(E)-4-(ethylthio)-2,2,5,5-tetramethyl-1-styryl-2,5-dihydro-1H-imidazole (in MeCN) |
MeCN | N Param.: 8.12 sN Param.: 0.88 | | Chem. Eur. J. 2023, , EarlyView 10.1002/chem.202302764 |
(E)-4-(benzylthio)-2,2,5,5-tetramethyl-1-styryl-2,5-dihydro-1H-imidazole (in CH2Cl2) |
dichloromethane | N Param.: 7.99 sN Param.: 0.98 | | Chem. Eur. J. 2023, , EarlyView 10.1002/chem.202302764 |
(S,E)-3-benzyl-1-methyl-4-styryl-1,4-diazaspiro[4.4]nonan-2-one |
MeCN | N Param.: 7.92 sN Param.: 1.07 | | Angew. Chem. Int. Ed. 2012, 51, 5739-5742 10.1002/anie.201201240 |
(E)-4-(ethylthio)-2,2,5,5-tetramethyl-1-(3-phenylbut-1-en-1-yl)-2,5-dihydro-1H-imidazole (in MeCN) |
MeCN | N Param.: 7.92 sN Param.: 0.73 | | Chem. Eur. J. 2023, , EarlyView 10.1002/chem.202302764 |
(E)-13-(ethylthio)-6-styryl-6,12-diazadispiro[4.1.47.25]tridec-12-ene (in MeCN) |
MeCN | N Param.: 7.79 sN Param.: 0.87 | | Chem. Eur. J. 2023, , EarlyView 10.1002/chem.202302764 |
2-((2,2,5,5-tetramethyl-1-styryl-2,5-dihydro-1H-imidazol-4-yl)thio)acetonitrile (in MeCN) |
MeCN | N Param.: 7.74 sN Param.: 0.87 | | Chem. Commun. 2023, 59, 8091-8084 10.1039/d3cc01912h |
(S,E)-5-benzyl-2,2,3-trimethyl-1-styrylimidazolidin-4-one |
MeCN | N Param.: 7.20 sN Param.: 1.14 | | Angew. Chem. Int. Ed. 2012, 51, 5739-5742 10.1002/anie.201201240 |