Abstract
Abstract An equimolar reaction of thiocyanoacetic esters with aldehydes in the presence of potassium fluoride or carbonate leads to a stereoisomeric mixture of cis and trans isomers of 5-substituted 4-alkoxycarbonyl-2-carbamoylimino1,3-oxathiolanes. Several of them were separated into two isomeric forms, whose geometrical configurations were determined by means of nuclear magnetic resonance technique. The vicinal coupling constant between the 4-and 5-protons is consistently larger for the cis forms than for the trans. In the case of the 5-aryl derivatives, the signals of the alkoxycarbonyl group appear at higher field for the cis isomers than for the trans. The composition ratios of cis and trans isomers of the oxathiolanes prepared are determined. Infrared data of the cis and trans oxathiolanes are also reported.
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