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

W.A. Loughlin; C.C. Rowen; P.C. Healy

doi:10.1039/B107705H

Back

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 article

Peer reviewed

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

W.A. Loughlin, C.C. Rowen and P.C. Healy

Journal of the Chemical Society, Perkin Transactions 2, (2), pp.296-302

2002

DOI: https://doi.org/10.1039/B107705H

Files and links (1)

url

Link to Published Version *Subscription may be requiredView

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.

Details

Title: 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
Authors/Creators: W.A. Loughlin (Author/Creator) - Griffith University
C.C. Rowen (Author/Creator) - Griffith University
P.C. Healy (Author/Creator) - Griffith University
Publication Details: Journal of the Chemical Society, Perkin Transactions 2, (2), pp.296-302
Publisher: Chemical Society
Identifiers: 991005543767907891
Murdoch Affiliation: Murdoch University
Language: English
Resource Type: Journal article

Metrics

62 Record Views