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Investigations into the reaction of the lithium enolate of cyclohexanone and phenyl vinyl sulfoxide: A simple synthesis of a bicyclo[4.2.0]octan-1-ol

Loughlin, W.A., Rowen, C.C.ORCID: 0000-0003-4490-9542 and Healy, P.C. (2002) Investigations into the reaction of the lithium enolate of cyclohexanone and phenyl vinyl sulfoxide: A simple synthesis of a bicyclo[4.2.0]octan-1-ol. Journal of the Chemical Society, Perkin Transactions 2 (2). pp. 296-302.

Link to Published Version: https://doi.org/10.1039/B107705H
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Abstract

The enolate generated from cyclohexanone and LDA at -78° C in THF reacts with (±)-phenyl vinyl sulfoxide to give the novel sulfinylbicyclo[4.2.0]octanols 1-3 and monoalkylated sulfoxide 4. The effects of changes in temperature, concentration, and reaction time were studied. By accurate control of temperature, concentration, and reaction time the ratio of bicyclooctanols 1-3 to monoalkylated sulfoxide 4 obtained was 95 : 5. The bicyclooctanols 1-3 were characterised as the sulfones 5 and 6. The relative stereochemistries of the bicyclooctanols 1-3 were established by X-ray structural determination.

Item Type: Journal Article
Publisher: Chemical Society
Copyright: © 2002 The Royal Society of Chemistry
URI: http://researchrepository.murdoch.edu.au/id/eprint/49205
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