76583-58-9Relevant academic research and scientific papers
Merostabilization of Biradicaloid Intermediates as a Factor in Determining Rates and Regioselectivity in Cycloaddition Reactions of Reissert Hydrofluoroborate Salts with Alkenes and Alkynes.
McEwen, William E.,Wang Huang, Irene C.,Cartaya Marin, Claudia P.,McCarty, Frances,Marmugi Segnini, Elba,et al.
, p. 3098 - 3105 (2007/10/02)
Reactions of 2-benzoyl-1,2-dihydroisoquinaldonitrile hydrofluoroborate with ethylene, acetylene, 1-hexyne, 1-phenylpropene, and cis-stilbene have been carried out.Also, reactions of 2-benzoyl-1-cyano-1,2-dihydrophthalazine and 2-benzoyl-1,2,3,4-tetrahydroisoquinaldonitrile hydrofluoroborates, respectively, with dimethyl acetylenedicarboxylate and with ethyl phenylpropiolate have been effected.The structures of most of the products have been established by unambiguous, independent syntheses.The kinetics of these reactions and of several additional ones reported previously have been measured.Arguments are presented that the rate and orientation data of these particular cycloaddition reactions are better rationalized by invoking the concept of the formation of merostabilized biradicaloid intermediates than by invoking the concept of orbital symmetry allowed concerted ring closures.
Substituent Effects in the Cycloaddition Reactions of Reissert Hydrofluoroborate Salts with Alkenes
McEwen, William E.,Hernandez, Maria Alcira,Ling, Chei-Fei,Marmugi, Elba,Padronaggio, Regina M.,et al.
, p. 1656 - 1662 (2007/10/02)
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.
