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Communication | Regular issue | Vol 26, No. 7, 1987, pp.1785-1788
Published online, 1st January, 1970
DOI: 10.3987/R-1987-07-1785
Preparation of Dihydrothiopyran-3-ones by Aldol Condensation of Diketo Sulfides and Acid-catalyzed Rearrangement of Ketol Intermediates Leading to Thiolan-3-one Derivatives

Juzo Nakayama, Keiko Hidaka, and Masamatsu Hoshino

*Department of Chemistry, Faculty of Science, Saitama University, Saitama, Saitama 338-8570, Japan


Acid-catalyzed intramolecular aldol condensation of diketo sulfides generally affords 2,6-dihydrothiopyran-3-ones and/or their 2,4-dihydro isomers in good yields. The ketol intermediates, in a few cases, undergo sulfur-participated rearrangement to give thiolan-3-one derivatives in addition to dihydrothiapyranones.