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E-Olefins: Reaction of Nitrones with Free and Pt-Coordinated Nitriles
J. Lasri, M. A. J. Charmier*, M. Haukka, A. J. L. Pombeiro*
Instituto Superior Técnico and Universidade Lusófona de Humanidades e Tecnologias, Lisbon, Portugal; Univeristy of Joensuu, Finland
24 April 2007 (online)
Organonitriles with acidic α-methylene protons showed interesting dual reactivity where both the methylene group and cyano group react under platinum catalysis. One important aspect is to use less reactive acyclic nitrones. Microwave irradiation was shown to significantly enhance the rate and yield of the reactions compared to normal reflux conditions. When precomplexed Pt-organonitrile substrates were used, the reaction showed a preference for the [3+2] cycloaddition product complexed to Pt(II). After prolonged heating the [3+2] adduct reverts to the thermodynamically favored cyanoalkene.