Collect. Czech. Chem. Commun. 1987, 52, 1764-1772

An advantageous synthesis of S-(2-propenyl) N-acylmonothiocarbamates by [3,3]-sigmatropic rearrangement of O-(2-propenyl) N-acylmonothiocarbamates

Peter Kutschy, Milan Dzurilla, Dušan Koščík and Pavol Kristian

Department of Organic Chemistry and Biochemistry, P. J. Šafárik University, 041 67 Košice


Reaction of acetyl, benzoyl, 2-chlorobenzoyl, 3-phenylpropenoyl, 2-naphthoyl, and 3-chloro-2-benzo[b]thienocarbonyl isothiocyanate with 2-propen-1-ol afforded the corresponding O-(2-propenyl) N-acylmonothiocarbamates which underwent [3,3]-sigmatropic rearrangement on heating in boiling benzene. The reaction represents a simple method for preparation of S-(2-propenyl) N-acylmonothiocarbamates in yields ranging from 50% to 98%.