Stereochemistry of cyclic compounds Communication 64. Stereochemistry of the oxidation and bromination of 4,5-dimethyl-4-cyclohexene-cis-1,2-dicarboxylic acid and its anhydride

Conclusions A study was made of the oxidation and bromination of 4,5-dimethyl-4-cyclohexene-cis-1,2-dicarboxylic acid (I) and its anhydride (II), and proof is given for the configurations of the then formed-epoxy anhydride (III), 5-hydroxy and 5-bromo-lactone acids (IV) and (V), and cis-glycol (IX). On the basis of the results of the acid hydrolysis of the trans-dibromo anhydride (VI) it is suggested that the bromine atoms in this compound have a diaxial arrangement.Translated from Izvestiya Akademii Nauk SSSR, Seriya Khimicheskaya, No. 4, pp. 689–695, April, 1966