61838-57-1Relevant academic research and scientific papers
Thermal rearrangements of bis-allenyl thiosulfonates. Synthesis of novel thienothiophene and thieno-oxathiine derivatives
Birsa, Mihail L.,Cherkinsky, Marina,Braverman, Samuel
, p. 9615 - 9619 (2002)
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.
