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Communication | Regular issue | Vol 36, No. 6, 1993, pp.1213-1215
Published online, 1st January, 1970
DOI: 10.3987/COM-93-6349
Novel Reactions of Carbohydrate Dithianes: 1,4-Dithiepins via a 1,4-Alkoxy Relay

Sherman T. Waddell,* Timothy A. Blizzard, and George A. Doss

*Merck Research Laboratories, 50G-231, P.O. Box 2000 Rahway, NJ 07065, U.S.A.

Abstract

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.