Permanganate peroxidation of cyclohexene. III. Hydroxide ion and salt effect studies

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Abstract
Good yields of cis-1,2-cyclohexanediol were formed by the reaction of cyclohexene and aqueous potassium permanganate under turbulent stirring conditions only in the presence of low concentrations of sodium hydroxide. Larger amounts had no further benefit or were deleterious. The lack of sensitivity to low concentrations of hydroxide ion indicated that its benefit is to inhibit acid promoted oxidations. There was no indication of its participation in the mechanism of glycol formation. The addition of the neutral salts, sodium sulfate or sodium nitrate, caused a decrease in glycol yields presumably due to a positive salt effect on a secondary negative ion – negative ion reaction, which formed other oxidation products. Stoichiometric amounts of hydroxide and potassium ions were not isolated as reaction products due to interaction with the hydrated manganese dioxide in a 1:2 ratio. The mechanisms in acidic and basic solutions appear to be quite different. A mechanism for basic solutions is suggested.

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