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

S. Braverman, E. V.K. Suresh Kumar, M. Cherkinsky, M. Sprecher, I. Goldberg

Research output: Contribution to journalArticlepeer-review

19 Scopus citations


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(methylene)cyclobutenes, and to stabilize the latter. The electron withdrawing group substitution on the exocyclic methylene extremities proved more effective than similar substitution on the endocyclic double bond.

Original languageEnglish
Pages (from-to)3547-3557
Number of pages11
Issue number14
StatePublished - 4 Apr 2005

Bibliographical note

Funding Information:
The financial support of this study by the Israel Science Foundations is gratefully acknowledged.


  • Bis(methylene)cyclobutenes
  • Diallenes
  • [2,3]-Sigmatropic rearrangements


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