Oxidation of meta- and para-substituted 2-phenyl-3-aryl thiazolidin-4-ones with Oxone at room temperature in methanol typically resulted in the formation of a mixture of diastereomeric sulfoxides. The ratio of diastereomers can be determined by integration of the hydrogen on C2 of the thiazolidin-4-one ring. Changing the reaction solvent to either acetone or acetonitrile in most cases yielded a single diastereomer. This solvent-based diastereoselectivity was further evaluated for a series of meta- and para-substituted 2-trichloromethyl-3-aryl-thiazolidin-4-ones, which yielded similar results.

Diastereoselectivity of oxone-based oxidations of 1,3 thiazolidin-4-ones to sulfoxides

Macromolecular Chemistry: The Second Century

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ACS Spring 2020 National Meeting & Expo

The official archive and repository for all ACS Meetings & Expositions abstracts and select posters or presentations.