Tetrahedron

γ-lactones and γ-thiolactones—I: A novel route to 6-oxabicyclo [3.2. 1] octan-7-one and 6-thiabicyclo [3.2. 1] octan-7-one derivatives

B Bochwic, A Frankowski

Index: Bochwic,B.; Frankowski,A. Tetrahedron, 1968 , vol. 24, p. 6653 - 6662

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Citation Number: 3

Abstract

Acetolysis of the adduct of diethoxyoxophosphoranesulphenyl chloride (I) and cyclohexene- 4-carboxylic acid chloride (IV), yields, via an intramolecular reaction, nearly equal amounts of 4-acetylthio-6-oxabicyclo [3.2. 1] octan-7-one (XIV) and 4-acetoxy-6-thiabicyclo [3.2. 1] octan-7-one (XVIII) and accounts for about 90% of the products. The 4-acetylthio group in XIV and the 4-acetoxy group in XVIII occupy axial positions. The results testify to the high ...