Please use this identifier to cite or link to this item: https://doi.org/10.1021/jo991776p
Title: Acylthioketene-thioacylketene-thiet-2-one rearrangements
Authors: Ammann, J.R.
Flammang, R.
Wong, M.W. 
Wentrup, C.
Issue Date: 5-May-2000
Citation: Ammann, J.R., Flammang, R., Wong, M.W., Wentrup, C. (2000-05-05). Acylthioketene-thioacylketene-thiet-2-one rearrangements. Journal of Organic Chemistry 65 (9) : 2706-2710. ScholarBank@NUS Repository. https://doi.org/10.1021/jo991776p
Abstract: 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.
Source Title: Journal of Organic Chemistry
URI: http://scholarbank.nus.edu.sg/handle/10635/75524
ISSN: 00223263
DOI: 10.1021/jo991776p
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