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Note | Regular issue | Vol 63, No. 4, 2004, pp.851-860
Published online, 30th January, 2004
DOI: 10.3987/COM-03-9980
Sequential Bromination-Rearrangement of Push-pull Thiazolidines Induced by Pyridinium Hydrobromide Perbromide under Homogenous Reaction Conditions

Rade Markovic,* Marija Baranac, and Zdravko Dzambaski

*Faculty of Chemistry, University of Belgrade, Studentski trg 16, P.O.Box 158, 11001 Belgrade, Serbia and Montenegro

Abstract

Regiospecific bromination-rearrangement of the 5-substituted 2-alkylidene-4-oxothiazolidine derivatives induced by pyridinium hydrobromide perbromide (PHBP) provides a new synthetic approach to the corresponding push-pull thiazolidines with two exocyclic double bonds. In comparison to a heterogenous alternative, this conversion, taking place in acetonitrile under homogenous reaction conditions, has the advantage of almost quantitative yields and a substantial rate enhancement.