Journal of the American Chemical Society

Stereochemistry of chlorination of thiane 1-oxides

J Klein, H Stollar

Index: Klein,J.; Stollar,H. Journal of the American Chemical Society, 1973 , vol. 95, p. 7437 - 7444

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Citation Number: 19

Abstract

Abstract: The chlorination of thiane 1-oxides containing large substituents gave a-chloro sulfoxides with the chlorine atom in the axial and the oxygen atom in the equatorial position, independent of the configuration at the sulfur of the starting material. Thiane 1-oxides containing small substituents do not undergo a sulfur but, rather, a ring inversion to place the oxygen in the equatorial position before being halogenated axially at the a positions. ...