Abstract
The hydrobromic-acid-induced opening of the epoxide ring in the stereoisomeric 1-hydroxy(or -acetoxy)-2,3-epoxy- and 3-hydroxy(or -acetoxy)-1,2-epoxy-5α-cholestanes was investigated. The results are evaluated with regard to the tendency to ‘diaxial opening’ of the epoxide ring and the tendency of the nucleophile to attack at the carbon atom β with respect to the neighbouring group. The 2α,3α-epoxides give mixtures of diaxial and di-equatorial products, whereas 2β,3β-epoxides give only diaxial products. All products obtained from 1,2-epoxides are diaxial. In several instances, the epoxide ring is displaced by an appropriately oriented acetoxy-group.
Talk to us
Join us for a 30 min session where you can share your feedback and ask us any queries you have
Schedule a callMore From: Journal of the Chemical Society, Perkin Transactions 1
Disclaimer: All third-party content on this website/platform is and will remain the property of their respective owners and is provided on "as is" basis without any warranties, express or implied. Use of third-party content does not indicate any affiliation, sponsorship with or endorsement by them. Any references to third-party content is to identify the corresponding services and shall be considered fair use under The CopyrightLaw.
