Peroxy acids reaction with enol acetate

The preparation of Pans-1,2-cyclohexanediol by oxidation of cyclohexene with peroxyformic acid and subsequent hydrolysis of the diol monoformate has been described, and other methods for the preparation of both cis- and trans-l,2-cyclohexanediols were cited. Subsequently the trans diol has been prepared by oxidation of cyclohexene with various peroxy acids, with hydrogen peroxide and selenium dioxide, and with iodine and silver acetate by the Prevost reaction. Alternative methods for preparing the trans isomer are hydroboration of various enol derivatives of cyclohexanone and reduction of Pans-2-cyclohexen-l-ol epoxide with lithium aluminum hydride. cis-1,2-Cyclohexanediol has been prepared by cis hydroxylation of cyclohexene with various reagents or catalysts derived from osmium tetroxide, by solvolysis of Pans-2-halocyclohexanol esters in a manner similar to the Woodward-Prevost reaction, by reduction of cis-2-cyclohexen-l-ol epoxide with lithium aluminum hydride, and by oxymercuration of 2-cyclohexen-l-ol with mercury(II) trifluoro-acetate in the presence of ehloral and subsequent reduction. ... 

Oxidation of methyl ethyl ketone with a mixture of oxygen and ozone in CC14 at 20—50° C yields acetic acid, diacetyl (intermediate) and hydrogen peroxide [280]. The reaction is second order with a rate coefficient, k = 3.6 X 109 exp(—17,000/RT) 1 mole 1 s 1. The oxidation of the ketone under these conditions is a radical non-chain reaction. Peroxy radicals react faster by a termination reaction than by a propagation reaction at these temperatures. In aqueous solution, ozone oxidizes the ketone as well as the enol form of methyl ethyl ketone [281] and therefore acid accelerates the rate of oxidation. 

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