Collect. Czech. Chem. Commun.
1990, 55, 710-717
https://doi.org/10.1135/cccc19900710
Intramolecular cyclization of O-alkyl-N-(3-phenylpropenoyl)thiocarbamates catalyzed by boron trifluoride
Milan Dzurillaa, Peter Kutschya, Dušan Koščíka and Štefan Tomab
a Department of Organic Chemistry, P. J. Šafárik University, 041 67 Košice
b Department of Organic Chemistry, Komenský University, 842 15 Bratislava
Abstract
2-Alkoxy-6-phenyl-5,6-dihydro-4H-1,3-thiazin-4-ones, 6-phenyl-1,3-perhydrothiazine-2,4-dione and S-methyl N-(3-phenylpropenoyl)thiocarbamate are the products of intramolecular rearrangement of O-alkyl N-(3-phenylpropenoyl)thiocarbamates catalyzed by boron trifluoride; their formation depends on the nature of the alkyl group. The rearrangement was shown to proceed intermolecularly by investigating the reaction of O-methyl N-(3-phenylpropenoyl)thiocarbamate to an S-methyl ester by the method of a crossover experiment.
