2 H,13C, and 14C Labelling studies have shown that the reaction of 4β-acetoxy-3β-hydroxy-Δ5- and 3β-acetoxy-4β-hydroxy-Δ5-steroids with acetic acid to form 3β,6β-diacetoxy-Δ4-steroids involves an intramolecular rearrangement of the C-4 acetate to C-3 proceeding via a 3β,4β-dioxolanylium ion accompanied by SNi attack at C-6β by the incoming acetate.
J. R. Hanson and P. B. Reese, J. Chem. Soc., Perkin Trans. 1, 1985, 331 DOI: 10.1039/P19850000331
To request permission to reproduce material from this article, please go to the Copyright Clearance Center request page.
If you are an author contributing to an RSC publication, you do not need to request permission provided correct acknowledgement is given.
If you are the author of this article, you do not need to request permission to reproduce figures and diagrams provided correct acknowledgement is given. If you want to reproduce the whole article in a third-party publication (excluding your thesis/dissertation for which permission is not required) please go to the Copyright Clearance Center request page.
Read more about how to correctly acknowledge RSC content.
Please wait while we load your content...