DEOXIMATION OF OXIMES, SODIUM OXIMATES AND O-BENZOYLOXIMES WITH COPPER (II) CHLORIDE DIHYDRATE

Oximes, O-benzoyloximes and sodium salt of aldoximes and ketoximes wer e deoximated to their parent carbonyl compounds with copper (II) chlor ide dihydrate in acetonitrile as well as water. This method works well with both aldoximes and ketoximes without any risk of overoxidation i n the former case. In addition, sensitive groups like ester, acetamido , isolated as well as conjugated carbon-carbon double bond and phenoli c 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 enhance ment over that of oximes, and tolerance to hydrolytically labile ester and amide groups is also described.