Issue 8, 2001
From the journal:

Journal of the Chemical Society, Perkin Transactions 1

Cyclizations versus rearrangements in the reactions of some epoxyolefins with Lewis acids †

Lars Petterssona  and  Torbjörn Frejd*a  

* Corresponding authors

a Division of Organic Chemistry, Centre for Chemistry and Chemical Engineering, Lund University, P.O.B. 124, Lund, Sweden
E-mail: Torbjorn.Frejd@orgk1.lu.se
Fax: +46-46-2224119

Abstract

Treatment of various substituted epoxyolefins A: with BF3·OEt2 and other reagents that could be expected to induce carbocyclization to give cyclohexanes was investigated. It turned out that the general reaction of these systems was the epoxide to ketone rearrangement, while the carbocyclization was only a rare event. Only substrates carrying the allylsilane grouping underwent carbocyclization and in addition the protecting groups and the stereochemistry of the system had a decisive influence on whether ring closure or rearrangement were to take place.

Graphical abstract: Cyclizations versus rearrangements in the reactions of some epoxyolefins with Lewis acids [ ]

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Article information

DOI
https://doi.org/10.1039/B010101J
Article type
Paper
Submitted
18 Dec 2000
Accepted
29 Jan 2001
First published
02 Mar 2001

J. Chem. Soc., Perkin Trans. 1, 2001, 789-800

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Cyclizations versus rearrangements in the reactions of some epoxyolefins with Lewis acids

L. Pettersson and T. Frejd, J. Chem. Soc., Perkin Trans. 1, 2001, 789 DOI: 10.1039/B010101J

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