Tetrahedron

Electron depleted bis (methylene) cyclobutenes: sulfinyl and sulfonyl substitution

S Braverman, EVKS Kumar, M Cherkinsky, M Sprecher…

Index: Braverman; Suresh Kumar; Cherkinsky; Sprecher; Goldberg Tetrahedron, 2005 , vol. 61, # 14 p. 3547 - 3557

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Citation Number: 15

Abstract

Double [2, 3] sigmatropic rearrangements of bis (propargyl sulfenates) to bis (allenic sulfoxides) and of bis (propargyl sulfinates) to bis (allenic sulfones) are shown to be a convenient and effective method for the preparation of conjugated diallene systems bearing two electron withdrawing trihalomethyl sulfoxide or sulfone substituents either on C-1 and C- 6, or on C-3 and C-4. Such substituents are further shown to facilitate cyclization to bis ( ...