The Action of Bromine in Acetic Acid on Dihydropyran and Some of Its Derivatives

WA Bonner, PJ Werth Jr, M Roth

Index: Bonner,W.A. et al. Journal of Organic Chemistry, 1962 , vol. 27, p. 1575 - 1578

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Citation Number: 7

Abstract

The action of bromine in acetic acid on phenyl 2-tetrahydropyryl sulfide (11) results in the formation of di (4bromophenyl) disulfide (111) and a crystalline dibromide, CbH8O2Br2 (IV). As the latter had unusual chemical and pharmacological properties its structure establishment was undertaken. Reduction of IV with lithium aluminum hydride led to 2, 2- dibromo-1, 5-pentandi) 1 (VI), which could be readily hydrolyzed to 2-keto-l, 5-pentandiol ( ...