Novel Method of Oxidation by a Polymeric reagent Electrochemically Generated and Recycled in Situ. Facile Oxidation of Alcohols.

Article abstract of DOI:10.1021/jo01314a008

A polymeric reagent electrochemically generated from crosslinked poly-4-vinylpyridine hydrobromide (1) was found to oxidize secondary alcohols to give the corresponding ketones in the absence of electric current.The exhausted polymeric reagent was regenerated by electrochemical oxidation.Thus a mild method of oxidation was developed which involved an electrochemical process in the presence of 1.Secondary alcohols were oxidized by this method to give the corresponding ketones in high yields, and hydrogen was formed quantitatively as a second product.Since the exhausted polymeric reagent is regenerated by continuous electrochemical oxidation in situ, only a catalytic amount of 1 (based on the alcohol) is required for the reaction, and the method does not consume any chemical oxidant and does not produce any contaminating reduced product.The efficiency of the electric current was very high, and only a slight excess of electricity was required to obtain the ketones in satisfactory yields.This method may remove defects of conventional electroorganic processes such as difficulty in separation and recovery of the electrolytes.