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The isomerization of α-pinene oxide with Brønsted and Lewis acids

✍ Scribed by J. Kaminska; M. A. Schwegler; A. J. Hoefnagel; H. van Bekkum

Publisher
Elsevier Science
Year
2010
Tongue
English
Weight
542 KB
Volume
111
Category
Article
ISSN
0165-0513

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✦ Synopsis

Abstract

α‐Pinene oxide (2) is a very reactive substrate which isomerizes rapidly under the influence of acid catalysts. A large number of products can be formed from a single intermediate. Selectivity to the industrially important campholenic aldehyde can be achieved with metal‐halogen compounds, especially zinc chloride and zinc bromide. A possible explanation for this behaviour is offered, stipulating a stabilized carbenium‐ion intermediate. Protonic catalysts are typically highly active but unselective. No evidence was found for the earlier reported selectivity to campholenic aldehyde with zeolite catalysts.

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