AQUEOUS PERMANGANATE OXIDATIONS OF CYCLOALKENES TO CIS-GLYCOLS AND CIS TO TRANS CONVERSIONS

A series of cis-glycols including 1,2-cyclopentanediol, 1-methyl-1,2-c yclopentanediol, 1,2 dimethyl-1,2-cyclopentanediol, 1,2-cyclohexanedio l, 1-methyl-1,2 cyclohexanediol, 1,2-dimethyl-1,2-cyclohexanediol, 1,2 -cycloheptanediol, 1,2-cyclooctanediol, exo,exo-bicyclo[2.2.1]heptane -2,3-diol, and bicyclo[2.2.2]octane-2,3-diol have been prepared by per manganate oxidations of cycloalkenes using a turbulent stirring techni que. Conditions for the reactions, methods of purification, and yields are presented. Both hydroxide ion and an aqueous environment are high ly essential to the formation of glycols. Excessive solvent decreases yields. A procedure for converting certain cis- to trans-glycols is gi ven. A preparation for very pure Delta(9,10)-octalin is included.