Highly Selective Oxidative Cleavage of Aryl Substituted Olefins with Pyridinium Chlorochromate

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Abstract
After the initial studies on the oxidative properties of pyridinium chlorochromate (PCC) by Corey1 a little under a decade ago, there have been numerous studies which have revealed the versatility of this reagent for the mild and selective oxidation of a number of organic substrates2. Oxidative cleavage of multiple bonds by PCC is shown to be limited to deoxirnation reactions.3,4 In addition, highly activated linear and cyclic enolic carbon-carbon double bonds are reported to be oxiaized by this reagent yielding esters and lactones, respective1y.5 In general, however, pyridinium chlorochromate, in contrast to other oxidant derivatives of chromium(VI), has been reported inactive towards carbon-czrbon double bonds1 adn triple bonds.6 In the course of our studies on oxidative cyclization we have recently shown that tertiary γ-hyoroxy olefins on treatment with PCC give reasonable yields of γ-lactones, with loss of one carbon.7 This prompted us to examined in detail the conditions under which olefinic substrates would undergo oxidative cleavage with PCC. In this communication we report a highly selective oxidative cleavage of carbon-caroon double bonds bearing aryl suostituents with pyridinium chlorochromate.

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