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dc.contributor.authorAitken, R Alan
dc.contributor.authorLightfoot, Philip
dc.contributor.authorThomas, Andrew W
dc.date.accessioned2021-04-23T23:41:02Z
dc.date.available2021-04-23T23:41:02Z
dc.date.issued2020
dc.identifier.citationAitken , 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/10.1080/17415993.2020.1754418en
dc.identifier.issn1741-5993
dc.identifier.otherPURE: 267301396
dc.identifier.otherPURE UUID: ca6e3e19-608a-4bcf-bc94-daa6855b4990
dc.identifier.otherORCID: /0000-0001-7048-3982/work/72842033
dc.identifier.otherORCID: /0000-0001-6959-5311/work/72842506
dc.identifier.otherScopus: 85085016016
dc.identifier.otherWOS: 000531938400001
dc.identifier.urihttp://hdl.handle.net/10023/23086
dc.description.abstractA 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.
dc.format.extent19
dc.language.isoeng
dc.relation.ispartofJournal of Sulfur Chemistryen
dc.rightsCopyright © 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/10.1080/17415993.2020.1754418en
dc.subject1,3-oxathiolaneen
dc.subjectPyrolysisen
dc.subjectSulfoxideen
dc.subjectSulfoneen
dc.subjectX-ray structureen
dc.subjectQD Chemistryen
dc.subjectDASen
dc.subject.lccQDen
dc.titleSynthesis, structure and reactivity of some chiral benzylthio alcohols, 1,3-oxathiolanes and their S-oxidesen
dc.typeJournal articleen
dc.description.versionPostprinten
dc.contributor.institutionUniversity of St Andrews.School of Chemistryen
dc.contributor.institutionUniversity of St Andrews.EaSTCHEMen
dc.identifier.doihttps://doi.org/10.1080/17415993.2020.1754418
dc.description.statusPeer revieweden
dc.date.embargoedUntil2021-04-24


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