Thermal rearrangements of bis-allenyl thiosulfonates. Synthesis of novel thienothiophene and thieno-oxathiine derivatives |
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Authors: | Mihail L Birsa Marina Cherkinsky Samuel Braverman |
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Institution: | aDepartment of Chemistry, Bar-Ilan University, Ramat-Gan 52900, Israel |
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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-thieno3,4-d]1,2]oxathiine-3-oxide 8, 1H,3H-thieno3,4-c]thiophene-2,2-dioxide 9, and 3-alkyl-4-alkenylthiophene 10. A tentative reaction mechanism involving sequential sigmatropic rearrangements and cyclizations is suggested. |
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Keywords: | allenes sulfinates thiosulfonates rearrangements |
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