Electron depleted bis(methylene)cyclobutenes: sulfinyl and sulfonyl substitution |
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Authors: | S. Braverman E.V.K. Suresh Kumar M. Sprecher |
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Affiliation: | a Department of Chemistry, Bar-Ilan University, Ramat-Gan 52900, Israel b School of Chemistry, Tel Aviv University, Ramat Aviv 69978, Israel |
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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(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. |
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Keywords: | Bis(methylene)cyclobutenes Diallenes [2,3]-Sigmatropic rearrangements |
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