Enamines, Enamides, and Ynamides
| Name | Solvent |
Reactivity Parameters |
Classification |
Reference (title or year) |
|---|---|---|---|---|
1-(N-morpholino)cyclohexene  |
dichloromethane | N Param.: 11.40 sN Param.: 0.83 |  | J. Am. Chem. Soc. 2001, 123, 9500-9512 10.1021/ja010890y |
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-pyrrolidino)cyclopentene |
dichloromethane | N Param.: 15.91 sN Param.: 0.86 | | Chem. Eur. J. 2003, 9, 2209-2218 10.1002/chem.200204666 |
1-(N-piperidino)cyclopentene |
dichloromethane | N Param.: 15.06 sN Param.: 0.82 | | Chem. Eur. J. 2003, 9, 2209-2218 10.1002/chem.200204666 |
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-(N-morpholino)cyclopentene |
dichloromethane | N Param.: 13.41 sN Param.: 0.82 | | Chem. Eur. J. 2003, 9, 2209-2218 10.1002/chem.200204666 |
1-(phenylmethylamino)cyclopentene |
dichloromethane | N Param.: 12.90 sN Param.: 0.79 | | 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 |
morpholinoisobutylene |
dichloromethane | N Param.: 10.04 sN Param.: 0.82 | | Chem. Eur. J. 2003, 9, 2209-2218 10.1002/chem.200204666 |
N-vinylcarbazole |
dichloromethane | N Param.: 5.02 sN Param.: 0.94 | | Macromolecules 2002, 35, 5454-5458 10.1021/ma020306l |
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-(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)-beta-(N-morpholino)styrene |
dichloromethane | N Param.: 10.76 sN Param.: 0.87 | | 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 |
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 |
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 |
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 |
(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 |
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-piperidino)cyclohexene (in MeCN) |
MeCN | N Param.: 14.02 sN Param.: 0.76 | | J. Am. Chem. Soc. 2013, 135, 6579-6587 10.1021/ja401106x |
N-(1-phenylvinyl)acetamide |
MeCN | N Param.: 5.73 sN Param.: 0.97 | | Chem. Eur. J. 2012, 18, 5732-5740 10.1002/chem.201103519 |
N-(1-(p-tolyl)vinyl)acetamide |
MeCN | N Param.: 6.57 sN Param.: 0.91 | | Chem. Eur. J. 2012, 18, 5732-5740 10.1002/chem.201103519 |
N-(1-(4-methoxyphenyl)vinyl)acetamide |
MeCN | N Param.: 7.06 sN Param.: 0.85 | | Chem. Eur. J. 2012, 18, 5732-5740 10.1002/chem.201103519 |
N-(1-(4-chlorophenyl)vinyl)acetamide |
MeCN | N Param.: 5.60 sN Param.: 1.00 | | Chem. Eur. J. 2012, 18, 5732-5740 10.1002/chem.201103519 |
benzyl (1-phenylvinyl)carbamate |
MeCN | N Param.: 6.21 sN Param.: 0.87 | | Chem. Eur. J. 2012, 18, 5732-5740 10.1002/chem.201103519 |
N-(1-phenylvinyl)benzamide |
MeCN | N Param.: 5.44 sN Param.: 1.00 | | Chem. Eur. J. 2012, 18, 5732-5740 10.1002/chem.201103519 |
N-(1-(naphthalen-2-yl)vinyl)acetamide |
MeCN | N Param.: 6.28 sN Param.: 0.95 | | Chem. Eur. J. 2012, 18, 5732-5740 10.1002/chem.201103519 |
N-(3,4-dihydronaphthalen-1-yl)acetamide |
MeCN | N Param.: 4.91 sN Param.: 0.87 | | Chem. Eur. J. 2012, 18, 5732-5740 10.1002/chem.201103519 |
N-(cyclohex-1-en-1-yl)acetamide |
MeCN | N Param.: 5.64 sN Param.: 0.79 | | Chem. Eur. J. 2012, 18, 5732-5740 10.1002/chem.201103519 |
N-(cyclopent-1-en-1-yl)acetamide |
MeCN | N Param.: 7.06 sN Param.: 0.87 | | Chem. Eur. J. 2012, 18, 5732-5740 10.1002/chem.201103519 |
N-(3,3-dimethylbut-1-en-2-yl)acetamide |
MeCN | N Param.: 4.61 sN Param.: 0.98 | | Chem. Eur. J. 2012, 18, 5732-5740 10.1002/chem.201103519 |
(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 |
(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 |
(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 |
(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 |
(2S,5S)-5-benzyl-2-(tert-butyl)-3-methyl-1-((E)-styryl)imidazolidin-4-one |
MeCN | N Param.: 5.80 sN Param.: 0.87 | | Angew. Chem. Int. Ed. 2012, 51, 5739-5742 10.1002/anie.201201240 |
N-benzyl-N-(but-1-yn-1-yl)-4-methylbenzenesulfonamide |
dichloromethane | N Param.: 5.16 sN Param.: 0.85 | | Angew. Chem. Int. Ed. 2014, 53, 4968-4971 10.1002/anie.201402055 |
N-benzyl-N-((2-methoxyphenyl)ethynyl)-4-methylbenzenesulfonamide |
dichloromethane | N Param.: 4.40 sN Param.: 0.86 | | Angew. Chem. Int. Ed. 2014, 53, 4968-4971 10.1002/anie.201402055 |
4-methyl-N-(2-phenylethynyl)-N-(phenylmethyl)benzenesulfonamide |
dichloromethane | N Param.: 3.85 sN Param.: 0.84 | | Angew. Chem. Int. Ed. 2014, 53, 4968-4971 10.1002/anie.201402055 |
1-(phenylethynyl)pyrrolidin-2-one |
dichloromethane | N Param.: 3.12 sN Param.: 0.85 | | Angew. Chem. Int. Ed. 2014, 53, 4968-4971 10.1002/anie.201402055 |
(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-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 |
(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-(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-(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 |
(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 |
(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-(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 |
(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)-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 |
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 |
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-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-((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 |
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 |
2-((2,2,5,5-tetramethyl-1-styryl-2,5-dihydro-1H-imidazol-4-yl)thio)acetonitrile (in CH2Cl2) |
dichloromethane | N Param.: 7.06 sN Param.: 1.11 | | 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. 2024, 30, e202302764 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. 2024, 30, e202302764 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. 2024, 30, e202302764 10.1002/chem.202302764 |
(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. 2024, 30, e202302764 10.1002/chem.202302764 |
(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. 2024, 30, e202302764 10.1002/chem.202302764 |
(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. 2024, 30, e202302764 10.1002/chem.202302764 |
(E)-2,2,3,5,5-pentamethyl-1-styrylimidazolidin-4-one (in MeCN) |
MeCN | N Param.: 7.10 sN Param.: 0.82 | | Chem. Eur. J. 2024, 30, e202302764 10.1002/chem.202302764 |
(E)-2,2,3,5,5-pentamethyl-1-styrylimidazolidine-4-thione (in MeCN) |
MeCN | N Param.: 6.49 sN Param.: 0.83 | | Chem. Eur. J. 2024, 30, e202302764 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. 2024, 30, e202302764 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. 2024, 30, e202302764 10.1002/chem.202302764 |