Abstract
Benzylic and allylic ethers are oxidized by 2,3-dichloro-5,6-dicyanobenzoquinone (DDQ) to give the corresponding carbonyl containing compounds (aldehydes and ketones) and alcohols. The reaction proceeds readily with ethers bearing activating groups. Primary ethers are further oxidized with excess DDQ giving the corresponding esters. Mechanisms for these processes are proposed, based on nuclear magnetic resonance and stoichiometric analyses. Keywords: dehydrogenation, allylic and benzylic ethers.
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