Studies of the cis-trans Isomerization of 3-Aryl-1,2,3-oxathiazolidine-2-oxides

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Abstract
The isomerization of the cis- or trans-3-aryl-1,2,3-oxathiazolidine-2-oxides was investigated under various conditions. The isomerization proceeded in carbon tetrachloride, chloroform, and benzyl chloride solutions at a low temperature. On the other hand, in other organic solvents, such as benzene, acetone, pyridine, N,N-dimethylformamide, and chlorobenzene, isomerization did not occur. The results can be explained by the mechanism which yields the open-chain halosulfamic acid anion by the attack of a halogen ion on the 5-position. The anion can close to cis- or trans-oxathiazolidine.