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Australian Journal of Chemistry Australian Journal of Chemistry Society
An international journal for chemical science
RESEARCH ARTICLE

Favorskii Rearrangement of Pulegone Dibromide and Pulegone Epoxide

SA Achmad and GWK Cavill

Australian Journal of Chemistry 16(5) 858 - 868
Published: 1963

Abstract

A stereospecific Favorskii rearrangement of pulegone dibromide, from D-pulegone, gives the trans-pulegenic acid which is converted into the corresponding bicyclic γ-lactone (V), a useful intermediate for the synthesis of the cyclopentanoid monoterpenes. A stereospecific rearrangement of pulegone epoxide (VIIa) yields the lactone (V), together with the trans,trans-hydroxyacid (VIIIb). A nonstereo-specific Favorskii rearrangement of the dibromide gives a mixture of the trans- and cis-pulegenic acids, but a comparable rearrangement of the epoxide gives the hydroxyacids of type (X). Mechanisms for these transformations are discussed.

https://doi.org/10.1071/CH9630858

© CSIRO 1963

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