
%0 Journal Article
%A Achmad, SA 
%A Cavill, GWK 
%T Favorskii Rearrangement of Pulegone Dibromide and Pulegone Epoxide
%J Australian Journal of Chemistry
%D 1963/10/01
%V 16
%N 5
%P 858-868
%K 
%R https://doi.org/10.1071/CH9630858
%U https://www.publish.csiro.au/paper/CH9630858 
%X A stereospecific Favorskii rearrangement of pulegone dibromide, from D-pulegone, gives the trans-pulegenic acid which is converted into the corresponding bicyclic &#947;-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. 
