
TY  - JOUR
A1  - Haynes, RK 
T1  - Lewis-acid-catalysed oxygenation of 1,1'-bicyclohexenyl and &#945;-terpinene. Reactions in dichloromethane and liquid sulphur dioxide
JF  - Australian Journal of Chemistry
JO  - Aust. J. Chem.
Y1  - 1978
VL  - 31
IS  - 1
SP  - 131
EP  - 138
KW  - 
UR  - https://doi.org/10.1071/CH9780131 
N2  - 1,1'-Bicyclohexenyl and &#945;-terpinene are converted into the corresponding cyclic peroxides in the presence of oxygen and Lewis acids in dichloromethane. In liquid sulphur dioxide under oxygen, the . major product from 1,1'-bicyclohexenyl in the presence of SnCl4, SbF5, and SbCl5, is the corresponding cyclic sulphone, whereas the cyclic peroxide is almost exclusively formed in this medium with MoCl5, WCl6 and VOCl3. Under the same conditions, &#945;-terpinene is quantitatively oxygenated in a dark reaction, in the absence of added Lewis acids. In a 1 : 1 dichloromethane-sulphur dioxide medium, ergosteryl acetate requires irradiation for conversion into the corresponding peroxide. Mechanistic interpretations of these observations are presented. 
ER  -

