Facile synthesis of thietanes via ring expansion of thiiranes?

Organic & Biomolecular Chemistry Pub Date: 2016-12-13 DOI: 10.1039/C6OB02387H

Abstract

Thietanes are pharmaceutically important cores of some biological compounds and intermediates of organic synthesis. Various thietanes were prepared from thiiranes via ring expansion through a reaction with trimethyloxosulfonium iodide in the presence of sodium hydride. The reaction process is a nucleophilic ring-opening reaction of thiiranes with dimethyloxosulfonium methylide, generated from trimethyloxosulfonium iodide and sodium hydride, and subsequent intramolecular displacement (cyclization) of thiolates to the dimethyloxosulfonium moiety. The current method provides a new strategy for efficient preparation of thietanes from readily available thiiranes.

Graphical abstract: Facile synthesis of thietanes via ring expansion of thiiranes
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