Files in this item
Synthesis, structure and reactivity of some chiral benzylthio alcohols, 1,3-oxathiolanes and their S-oxides
Item metadata
dc.contributor.author | Aitken, R Alan | |
dc.contributor.author | Lightfoot, Philip | |
dc.contributor.author | Thomas, Andrew W | |
dc.date.accessioned | 2021-04-23T23:41:02Z | |
dc.date.available | 2021-04-23T23:41:02Z | |
dc.date.issued | 2020 | |
dc.identifier | 267301396 | |
dc.identifier | ca6e3e19-608a-4bcf-bc94-daa6855b4990 | |
dc.identifier | 85085016016 | |
dc.identifier | 000531938400001 | |
dc.identifier.citation | 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 | en |
dc.identifier.issn | 1741-5993 | |
dc.identifier.other | ORCID: /0000-0001-7048-3982/work/72842033 | |
dc.identifier.other | ORCID: /0000-0001-6959-5311/work/72842506 | |
dc.identifier.uri | https://hdl.handle.net/10023/23086 | |
dc.description.abstract | 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. | |
dc.format.extent | 19 | |
dc.format.extent | 3257849 | |
dc.language.iso | eng | |
dc.relation.ispartof | Journal of Sulfur Chemistry | en |
dc.subject | 1,3-oxathiolane | en |
dc.subject | Pyrolysis | en |
dc.subject | Sulfoxide | en |
dc.subject | Sulfone | en |
dc.subject | X-ray structure | en |
dc.subject | QD Chemistry | en |
dc.subject | DAS | en |
dc.subject.lcc | QD | en |
dc.title | Synthesis, structure and reactivity of some chiral benzylthio alcohols, 1,3-oxathiolanes and their S-oxides | en |
dc.type | Journal article | en |
dc.contributor.institution | University of St Andrews. School of Chemistry | en |
dc.contributor.institution | University of St Andrews. EaSTCHEM | en |
dc.identifier.doi | https://doi.org/10.1080/17415993.2020.1754418 | |
dc.description.status | Peer reviewed | en |
dc.date.embargoedUntil | 2021-04-24 |
This item appears in the following Collection(s)
Items in the St Andrews Research Repository are protected by copyright, with all rights reserved, unless otherwise indicated.