Thermal rearrangements of bis-allenyl thiosulfonates. Synthesis of novel thienothiophene and thieno-oxathiine derivatives

Mihail L. Birsa, Marina Cherkinsky, Samuel Braverman

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Abstract

The synthesis and thermal rearrangement of bis-allenyl thiosulfonates are described. Bis-γ,γ-disubstituted allenyl thiosulfonates have been prepared by disproportionation of the corresponding allenesulfinic acids. On heating, these compounds unexpectedly rearrange to a mixture of 1H,3H-thieno[3,4-d][1,2]oxathiine-3-oxide 8, 1H,3H-thieno[3,4-c]thiophene-2,2-dioxide 9, and 3-alkyl-4-alkenylthiophene 10. A tentative reaction mechanism involving sequential sigmatropic rearrangements and cyclizations is suggested.

Original languageEnglish
Pages (from-to)9615-9619
Number of pages5
JournalTetrahedron Letters
Volume43
Issue number52
DOIs
StatePublished - 23 Dec 2002

Bibliographical note

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

Keywords

  • Allenes
  • Rearrangements
  • Sulfinates
  • Thiosulfonates

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