Tetrahedron letters

The facile addition of fluorosulfuric acid to an epoxide

CS Poorker, J Kagan

Index: Poorker, Carol S.; Kagan, Jacques Tetrahedron Letters, 1985 , vol. 26, # 52 p. 6405 - 6408

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Citation Number: 13

Abstract

Abstract Fluorosulfuric acid, a very poor nucleophile, was found to add to several epoxides, yielding 1, 3, 2-dioxathiolane 2, 2-dioxides. These cyclic sulfates could also be obtained by reacting the epoxides with sulfur trioxide. The intermediacy of the fluorosulfate of a 1, 2-diol, which readily cyclized in base, has been demonstrated in one case.