When heated, 1,3-dithiane derivatives of common sugars which bear a mesylate at the 5-position (and are otherwise O-methylated) form 1,4-dithiepins by a novel mechanism in which ring expansion is coordinated with intramolecular relay of the 2-alkoxy group to the 5 position. Addition of a nucleophile such as azide to the reaction produces novel structures resulting from the trapping of intermediates along the pathway

Carbohydrate dithianes form 1,4-dithiepins through a novel mechanism, ring expansion coordinated with intramolecular relay of the 2-alkoxy group to the 5 position.

Paper

Novel Reactions of Carbohydrate Dithianes: 1,4‐Dithiepins via a 1,4‐ Alkoxy Relay.

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