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Issue 14, 1997
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Synthesis and pyrolytic behaviour of thiazolidin-2-one 1,1-dioxides

Abstract

Four examples of the chiral thiazolidin-2-one 1,1-dioxides 5 have been prepared by reaction of the appropriate amino alcohols 11 with CS2 in aqueous sodium hydroxide to give the thiazolidine-2-thiones 12, followed by oxidation with KMnO4 under phase-transfer conditions in the presence of benzoic acid, either directly or via the thiazolidin-2-ones 13. Upon flash vacuum pyrolysis (FVP) at 650 °C, 5a–c decompose mainly by loss of SO2 to give an alkene and benzyl isocyanate together with other products from fragmentation of the N-benzyl group. A significant minor pathway involves net loss of CO2 and water to give the 2-phenyl-4,5-dihydrothiazoles 21 together with their aromatisation products 22 and 23. A mechanism for this new heterocyclic transformation is proposed involving initial expansion to a cyclic carbamic–sulfinic anhydride (2,1,4-oxathiazin-3-one 1-oxide). The fully assigned 13C NMR spectra are presented for 5, 12 and 13 and the 33S NMR spectrum has been obtained for 5c.

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Article type: Paper
DOI: 10.1039/A700521K
J. Chem. Soc., Perkin Trans. 1, 1997, 2139-2146

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    Synthesis and pyrolytic behaviour of thiazolidin-2-one 1,1-dioxides

    R. Alan Aitken, D. P. Armstrong, R. H. B. Galt and S. T. E. Mesher, J. Chem. Soc., Perkin Trans. 1, 1997, 2139
    DOI: 10.1039/A700521K

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