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Room Temperature Ring-Opening Cyclization Reactions of 2-Vinylaziridines with Isocyanates, Carbodiimides, and Isothiocyanates Catalyzed by [Pd(OAc)2]/PPh3

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journal contribution
posted on 23.08.2000, 00:00 by David C. D. Butler, Gyro A. Inman, Howard Alper
2-Vinylaziridines undergo cycloaddition reactions with various heterocumulenes, in the presence of [Pd(OAc)2] and PPh3, at room temperature and 1 atm pressure, regioselectively affording five-membered ring products in moderate to high yields. The mixture of stereoisomers obtained by reactions employing cis-1-butyl-2-vinyl-3-methylaziridine as the reactant provides evidence for a mechanism involving a η3−η1−η3 interconversion of a (π-allyl)palladium intermediate.