Journal of Organic Chemistry p. 1656 - 1662 (1981)
Update date:2022-08-05
Topics:
McEwen, William E.
Hernandez, Maria Alcira
Ling, Chei-Fei
Marmugi, Elba
Padronaggio, Regina M.
et al.
An evaluation of substitutent effects has been undertaken of the cycloaddition of 2-aroyl-1,2-dihydroisoquinaldonitrile hydrofluoroborates (5) with substituted ethyl cinnamates, styrenes, stilbenes, and ethylenes.The cinnamates give mixtures of 2-(1-isoquinolyl)-3,5-diaryl-4-carbethoxypyrroles.The stilbenes give mixtures of 2-(1-isoquinolyl)-3,4,5-triarylpyrroles, but the styrenes give only 2-(1-isoquinolyl)-3,5-diarylpyrroles. 1-Hexene and cyclohexene undergo cycloaddition with 5 (Y=H) readily, but 2-heptene does not.The rates of many these reactions have been determined.The implications of the results with respect to the mechanism of reaction are discussed.
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Doi:10.1016/S0040-4020(01)97941-4
(1981)Doi:10.1021/jo00140a021
(1982)Doi:10.1016/S0040-4039(00)86829-X
(1982)Doi:10.1246/cl.1982.763
(1982)Doi:10.1139/v82-181
(1982)Doi:10.1039/jr9490000703
(1949)