Sequential intermediates in the base-catalyzed conversion of bis(π-conjugated propargyl) sulfones to 1,3-dihydrobenzo- and naphtho[c]thiophene-2,2-dioxides

Yossi Zafrani, Hugo E. Gottlieb, Milon Sprecher, Samuel Braverman

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Abstract

In a recent article, we reported on the base-catalyzed rearrangements of dipropargyl selenides, -Sulfides, -sulfoxides, and -sulfones that eventually lead to polycyclic aromatic products. In the present work, we report on the first isolation and characterization of the thiophene dioxide intermediates 5b,c from a mild tandem isomerization/cyclization/aromatization of bis(π-conjugated propargyl) sulfones. Monoallene 2b,c and diallene 3b intermediates were also identified by NMR. A kinetic study of the rearrangement of 1a-c revealed that the unusual facile tandem process is highly dependent on the nature of γ-substitution.

Original languageEnglish
Pages (from-to)10166-10168
Number of pages3
JournalJournal of Organic Chemistry
Volume70
Issue number24
DOIs
StatePublished - 25 Nov 2005

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