Synthesis of Conjugated Diallenes by Double [2,3]-Sigmatropic Rearrangement of Conjugated Diyne Trichloromethanesulfenates

The preparation of several 2,4-diyne-l,6-diols and their esterification with trichloromethanesulfenyl chloride is described. The thus generated bis-propargylic trichloromethanesulfenates undergo spontaneous double [2,3]-sigmatropic rearrangement which leads to the formation of conjugated diallenic t...

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Bibliographic Details
Published inSynthetic communications Vol. 29; no. 15; pp. 2629 - 2637
Main Authors Raj, C. Paul, Braverman, S.
Format Journal Article
LanguageEnglish
Published NEW YORK Taylor & Francis Group 01.08.1999
Marcel Dekker Inc
Subjects
Chemistry
Chemistry, Organic
Physical Sciences
Science & Technology
SULFONES
BRIDGED DIALLENES
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Summary:The preparation of several 2,4-diyne-l,6-diols and their esterification with trichloromethanesulfenyl chloride is described. The thus generated bis-propargylic trichloromethanesulfenates undergo spontaneous double [2,3]-sigmatropic rearrangement which leads to the formation of conjugated diallenic trichloromethyl sulfoxides in good to excellent yields.
ISSN:0039-7911
1532-2432
DOI:10.1080/00397919908086424