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Acylthioketene-thioacylketene-thiet-2-one rearrangements
Journal of Organic Chemistry 2000 May 10
Flash vacuum thermolysis (FVT) of 6-aryl-1,3-dioxine-4-thiones 9 leads to the formation of acylthioketenes 10, which are characterized by Ar matrix IR spectroscopy as well as on-line tandem mass spectrometry. The thioketenes 10 undergo a 1,3-shift of the aryl group to generate thioacylketenes 11. Ketenes 11 cyclize to 3-aryl-thiet-2-ones 12, which are also characterized by matrix IR spectroscopy and tandem mass spectrometry. The thiet-2-ones 12 undergo two kinds of reaction under the FVT conditions: (i) cheletropic CO extrusion with formation of arylthioketenes 13, and (ii) cycloreversion to COS and arylacetylene.
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