
TY  - JOUR
A1  - Achmad, SA 
A1  - Cavill, GWK 
T1  - Favorskii Rearrangement of Pulegone Dibromide and Pulegone Epoxide
JF  - Australian Journal of Chemistry
JO  - Aust. J. Chem.
Y1  - 1963
VL  - 16
IS  - 5
SP  - 858
EP  - 868
KW  - 
UR  - https://doi.org/10.1071/CH9630858 
N2  - 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. 
ER  -

