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.
Aitken , R A , Henderson , S & Slawin , A M Z 2018 , ' Structure and thermal reactivity of some 2-substituted 1,3-oxathiolane S-oxides ' Journal of Sulfur Chemistry , vol. 39 , no. 4 , pp. 422-434 . https://doi.org/10.1080/17415993.2018.1449844
Journal of Sulfur Chemistry
© 2018 Informa UK Limited, trading as Taylor & Francis Group. This work has been made available online in accordance with the publisher’s policies. This is the author created accepted version manuscript following peer review and as such may differ slightly from the final published version. The final published version of this work is available at https://doi.org/10.1080/17415993.2018.1449844
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