Abstract
The reaction of cis- and trans-4-acylamino-3-hydroxythiophans with thionyl chloride was studied. It was found that chlorosulfites are initially formed with retention of the configuration of the starting compound. 2-Substituted 3a,4,6,6a-tetrahydrothieno[3,4-d]oxazoline is formed from trans-4-acylamino-3-chlorosulfitothiophans by thermal reaction or in the presence of pyridine, whereas trans-4-acylamino-3-chlorothiophans are obtained from cis-4-acylamino-3-chlorosulfitothiophans; both reactions proceed with inversion of configuration.
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