Unusual transformations in oxabicyclooctanones. An apparent oxypromoted electrocyclic opening involving fused cyclobutanols

A Hassner, S Naidorf-Meir, HE Gottlieb, F Frolow

Index: Hassner, Alfred; Naidorf-Meir, Simha; Gottlieb, Hugo E.; Frolow, Felix Tetrahedron Letters, 1990 , vol. 31, # 39 p. 5669 - 5672

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Citation Number: 2

Abstract

Abstract Reaction of oxabicyclooctanone 3 with nucleophiles involves not only cine substitution but ring opening to cyclobutenones which are capable of further transformations. With azide as a nucleophile, further reactions occur, among them an oxy-promoted electrocyclic cyclobutane opening, with final formation of 8, the structure of which was verified by X-ray diffraction.