Issue 0, 1970
From the journal:

Journal of the Chemical Society B: Physical Organic

Epoxidation of allylic alcohols with peroxy-acids. Attempts to define transition state geometry

P. Chamberlain,   M. L. Roberts  and  G. H. Whitham  

Abstract

In epoxidation of the conformationally biassed 5-t-butylcyclohex-2-enols by peroxybenzoic acid, higher cis-stereoselectivity and faster rate are found for the pseudo-equatorial than for the pseudo-axial alcohol. Cyclo-oct-2-en-1-ol is epoxidised with stereospecific introduction of the epoxy-group trans to hydroxy, and appropriate acyclic allylic alcohols show a preference for formation of the threo-epoxy-alcohol. A consistent interpretation of these results is advanced, based on the postulate that the preferred conformation of an allylic alcohol in the transition state for epoxidation is as in (XX).

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Article information

DOI
https://doi.org/10.1039/J29700001374
Article type
Paper

J. Chem. Soc. B, 1970, 1374-1381

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Epoxidation of allylic alcohols with peroxy-acids. Attempts to define transition state geometry

P. Chamberlain, M. L. Roberts and G. H. Whitham, J. Chem. Soc. B, 1970, 1374 DOI: 10.1039/J29700001374

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