Synthesis, structure and reactivity of some chiral benzylthio alcohols, 1,3-oxathiolanes and their S-oxides
MetadataShow full item record
A series of amino acid-derived chiral benzylthio alcohols have been prepared and characterised. A chiral mercapto alcohol derived from S-leucine has been used to form three chiral 2,4-disubstituted 1,3-oxathiolanes. One of these has been oxidised to the S-oxide and another to the S,S-dioxide. The cis and trans isomers have been characterised by 1H NMR in each case and it appears that thermal epimerisation at C-2 is possible at the sulfoxide oxidation state. The X-ray structure of major trans diastereomer of 2-phenyl-4-isobutyl-1,3-oxathiolane S,S-dioxide shows an envelope conformation with oxygen at the flap and an internal angle at sulfur of just 93.8°. This compound fragments upon flash vacuum pyrolysis at 700 °C to give SO2, benzaldehyde and 4-methylpent-1-ene.
Aitken , R A , Lightfoot , P & Thomas , A W 2020 , ' Synthesis, structure and reactivity of some chiral benzylthio alcohols, 1,3-oxathiolanes and their S -oxides ' , Journal of Sulfur Chemistry , vol. 41 , no. 4 , pp. 369-387 . https://doi.org/10.1080/17415993.2020.1754418
Journal of Sulfur Chemistry
Copyright © 2020 Informa UK Limited, trading as Taylor & Francis Group. This work has been made available online in accordance with publisher policies or with permission. Permission for further reuse of this content should be sought from the publisher or the rights holder. This is the author created accepted manuscript following peer review and may differ slightly from the final published version. The final published version of this work is available at https://doi.org/10.1080/17415993.2020.1754418
Items in the St Andrews Research Repository are protected by copyright, with all rights reserved, unless otherwise indicated.