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Tandem sigmatropic rearrangements and cyclizations of propargylic dialkoxy disulfides

โœ Scribed by Samuel Braverman; Tatiana Pechenick; Hugo E Gottlieb


Publisher
Elsevier Science
Year
2003
Tongue
French
Weight
157 KB
Volume
44
Category
Article
ISSN
0040-4039

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Tandem rearrangement, cyclization and ar
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The reactivity of some novel ฯ€-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 intermediat

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Facile preparation and rearrangement of
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Allylic dialkoxy disulfides were obtained in good yields and their reactivity has been investigated. Similarly to allylic sulfoxylates, these esters undergo double [2,3]-sigmatropic rearrangement to the appropriate vic-disulfoxides. The latter, being unstable, undergoes spontaneous rearrangement to

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The synthesis and reactivity of bis-g-substituted and unsubstituted propargylic sulfonium and selenonium salts under various basic conditions have been investigated. While the former compounds reacted only by [2,3]-sigmatropic rearrangement of the corresponding sulfur ylides, the latter salts exhibi