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Loughlin WA, McCleary MA. The formation of bicyclo[n.2.0]alkan-1-ols from the reaction of the lithium enolates of simple ketones and phenyl vinyl sulfoxide. Org Biomol Chem. 2003;1(8):1347-53doi: 10.1039/b208365e.
Loughlin, W. A., & McCleary, M. A. (2003). The formation of bicyclo[n.2.0]alkan-1-ols from the reaction of the lithium enolates of simple ketones and phenyl vinyl sulfoxide. Organic & biomolecular chemistry, 1(8), 1347-53. https://doi.org/10.1039/b208365e
Loughlin, Wendy A, and McCleary, Michelle A. "The formation of bicyclo[n.2.0]alkan-1-ols from the reaction of the lithium enolates of simple ketones and phenyl vinyl sulfoxide." Organic & biomolecular chemistry vol. 1,8 (2003): 1347-53. doi: https://doi.org/10.1039/b208365e
Loughlin WA, McCleary MA. The formation of bicyclo[n.2.0]alkan-1-ols from the reaction of the lithium enolates of simple ketones and phenyl vinyl sulfoxide. Org Biomol Chem. 2003 Apr 21;1(8):1347-53. doi: 10.1039/b208365e. PMID: 12929665.
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Org Biomol Chem. 2003 Apr 21;1(8):1347-53. doi: 10.1039/b208365e.

The formation of bicyclo[n.2.0]alkan-1-ols from the reaction of the lithium enolates of simple ketones and phenyl vinyl sulfoxide.

Organic & biomolecular chemistry

Wendy A Loughlin, Michelle A McCleary

Affiliations

  1. School of Science, Griffith University, Brisbane, QLD, 4111, Australia. [email protected]

PMID: 12929665 DOI: 10.1039/b208365e

Abstract

The enolates generated from cyclopentanone, cycloheptanone or cyclooctanone and LDA at -78 degrees C in THF react with (+/-)-phenyl vinyl sulfoxide under controlled conditions of temperature, reaction time, and concentration. Upon oxidation with MCPBA of the product mixtures, the novel sulfonylbicyclo[3.2.0]heptan-1-ols10-12,sulfonylbicyclo[5.2.0]-nonan-1-ols 16-18, and sulfonylbicyclo[6.2.0]decan-1-ols 21 and 22 in conjunction with alkylated ketones 8, 9, 15, 19 and 20 were obtained from the respective ketones. The enolate generated from cyclobutanone and LDA at -78 degrees C in THF reacts with (+/-)-phenyl vinyl sulfoxide and upon oxidation with MCPBA, the cyclohexanone 4 and monoalkylated cyclobutanone 5 were obtained. The ratio of bicyclo[n.2.0]alkan-1-ol to alkylated products varied with the ketone enolate, conversion of phenyl vinyl sulfoxide, time, temperature and concentration of reaction and the stability and steric strain of the final bicyclo[n.2.0]alkan-1-ol product.

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