Carbon-hydrogen bonds aryl ethers

Abnormal olefin arylation reactions which are of interest mechanistically and preparatively occur with some allylically substituted compounds. The ailylic esters and ethers appear normal and produce cinnamyl derivatives exclusively while ailylic alcohols and chlorides are abnormal. Ailylic alcohols and "arylpalladium acetates form 3-arylaldehydes from primary ailylic alcohols and 3-arylketones from secondary alcohols 3°). The mechanism of reaction apparently involves anti-Markovnikov addition of the palladium compound to the double bond followed by elimination of the hydrogen atom on the hydroxyl-bearing carbon rather than the benzylic hydrogen. This again would be elimination of the more electronegative hydrogen atom. 

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