Steric effects in the tetracyanoethylene catalysed methanolysis of some cyclohexane epoxides

Uyanik C. , Hanson J., Hitchcock P., Lazar M.

TETRAHEDRON, vol.61, no.17, pp.4323-4327, 2005 (Journal Indexed in SCI) identifier identifier

  • Publication Type: Article / Article
  • Volume: 61 Issue: 17
  • Publication Date: 2005
  • Doi Number: 10.1016/j.tet.2005.01.030
  • Title of Journal : TETRAHEDRON
  • Page Numbers: pp.4323-4327
  • Keywords: cyclohexane, TCNE, methanoloysis, epoxide, stereochemistry, STEREOCHEMISTRY

Abstract

The presence of a hydroxyl group has been shown to direct the regiochemistry and stereochemistry of the TCNE methanolysis of cyclohexane hydroxy-epoxides. alpha-Pinene epoxide underwent cleavage to form the 8-methyl ether of trans-sobrerol. (c) 2005 Elsevier Ltd. All rights reserved.