Reductive Acetoxylation on .alpha.,.alpha.\u27-dibromocycloalkanones by Ultrasonically Dispersed Mercury


The α,α\u27-dibromocycloalkanones of ring size 5-12 were reduced by ultrasonically dispersed mercury in acetic acid. Products were the corresponding cycloalkanone and -acetoxycycloalkanone. The ratio of these two is quite sensitive to ring size, and this fact is used to support the intermediate formation of 2-hydroxyallyl cations as precursors of the keto acetates. Molecular mechanics calculations support the proposed mechanism

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Last time updated on July 9, 2019

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