Deoximation of Oximes, Sodium Oximates, and O-Benzoyloximes with Copper (II) Chloride Dihydrate

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Abstract
Oximes, O-benzoyloximes and sodium salt of aldoximes and ketoximes were deoximated to their parent carbonyl compounds with copper (II) chloride dihydrate in acetonitrile as well as water. This method works well with both aldoximes and ketoximes without any risk of overoxidation in the former case. In addition, sensitive groups like ester, acetamido, isolated as well as conjugated carbon-carbon double bond and phenolic and ether linkages could survive the reaction conditions. The yields and reaction rates were increased in case of aromatic oximes when the reaction was carried out in aqueous acetonitrile. A novel deoximation procedure using sodium oximate which showed considerable rate enhancement over that of oximes, and tolerance to hydrolytically labile ester and amide groups is also described.