Structure and thermal reactivity of some 2-substituted 1,3-oxathiolane S-oxides

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Isomerisation of 2-benzylidene-1,3-dioxolane to 3-phenylbutyrolactone occurs readily under flash vacuum pyrolysis (FVP) conditions. 2-Diphenylmethyl-1,3-oxathiolane and 2-benzyl-1,3-oxathiolane have been prepared and the latter compound has been oxidised to the corresponding sulfoxide, whose structure and conformation is examined by 1H NMR, and to the sulfone whose X-ray structure is determined. 2-Benzylidene-1,3-oxathiolane is also prepared and the behaviour of the three S-oxidised oxathiolane derivatives upon FVP is examined. While extrusion of SOn to give ethene and a carbonyl compound predominates in all three cases, the sulfoxide also gives bis(2-hydroxyethyl) disulfide, most likely formed via thiirane S-oxide and 1,2-oxathietane.
Original languageEnglish
Pages (from-to)422-434
Number of pages13
JournalJournal of Sulfur Chemistry
Issue number4
Early online date20 Mar 2018
Publication statusPublished - 11 Jul 2018


  • 1,3-oxathiolane
  • Pyrolysis
  • Sulfoxide
  • Sulfone
  • X-ray structure


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