Tandem rearrangement, cyclization and aromatization of sulfur bridged propargylic systems

Samuel Braverman, Yossi Zafrani, Hugo E. Gottlieb

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25 Scopus citations

Abstract

The reactivity of some novel Π-conjugated bis-propargylic sulfides, sulfoxides and sulfones under basic conditions has been investigated. These compounds undergo isomerization to the corresponding diallenes, followed by a tandem cyclization and aromatization of the latter via a diradical intermediate. Surprisingly, we have found that the rate of the cyclization step was independent of the nature of the bridging functionality. (C) 2000 Elsevier Science Ltd.

Original languageEnglish
Pages (from-to)2675-2678
Number of pages4
JournalTetrahedron Letters
Volume41
Issue number15
DOIs
StatePublished - 8 Apr 2000

Bibliographical note

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

Funding

The financial support of this study by the Israel Science Foundation is gratefully acknowledged.

FundersFunder number
Israel Science Foundation

    Keywords

    • Cyclization
    • Diallenes
    • Diradicals
    • Diynes
    • Sulfur compounds

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