Tetrahedron Letters

A novel rearrangement of the adduct from CS-epoxide and dioxan-2-hydroperoxide

JM Harrison, TD Inch

Index: Harrison, John M.; Inch, Thomas D. Tetrahedron Letters, 1981 , vol. 22, p. 679 - 682

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Citation Number: 10

Abstract

Abstract Under mild conditions, nucleophiles add across the cyanide moiety of CS epoxide rather than opening the ring. With hydroxide ion in peroxide-free aqueous dioxan isomeric amides are obtained. Hydrolysis in peroxide containing dioxan affords a novel rearrangement involving carbon—carbon bond fission of the dioxan.