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Synthesis, structure and reactivity of some chiral benzylthio alcohols, 1,3-oxathiolanes and their S-oxides

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Aitken_2020_JSC_Synthesis_AAM.pdf (3.106Mb)
Date
2020
Author
Aitken, R Alan
Lightfoot, Philip
Thomas, Andrew W
Keywords
1,3-oxathiolane
Pyrolysis
Sulfoxide
Sulfone
X-ray structure
QD Chemistry
DAS
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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.
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
Publication
Journal of Sulfur Chemistry
Status
Peer reviewed
DOI
https://doi.org/10.1080/17415993.2020.1754418
ISSN
1741-5993
Type
Journal article
Rights
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
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  • University of St Andrews Research
URI
http://hdl.handle.net/10023/23086

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