Structure and thermal reactivity of some 2-substituted 1,3-oxathiolane S-oxides
Abstract
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.
Citation
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
Publication
Journal of Sulfur Chemistry
Status
Peer reviewed
ISSN
1741-5993Type
Journal article
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