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Tandem rearrangement, cyclization and aromatization of sulfur bridged propargylic systems

✍ Scribed by Samuel Braverman; Yossi Zafrani; Hugo E Gottlieb

Publisher
Elsevier Science
Year
2000
Tongue
French
Weight
109 KB
Volume
41
Category
Article
ISSN
0040-4039

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✦ Synopsis

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.

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## Abstract A variety of dihydroisobenzofuran derivatives has been prepared in good yields __via__ an interesting sequential reaction consisting of palladium‐catalyzed coupling, propargyl‐allenyl rearrangement, [4+2] cycloaddition and aromatization. A double‐coupling, rearrangement, [4+2] cycloaddi