Direct conversion of aldehydes into nitriles via O-phenylcarbamoylated aldoximes

Abstract

O-Arylcarbamoylated hydroxylamine tosylate reacts with aldehydes at room temperature to give the corresponding O-carbamoylated oximes. The reaction of carbamoylated hydroxylamine with aromatic aldehydes in THF or in toluene at reflux affords the corresponding nitriles and anilinium tosylate in high yield. Attempts to cyclize compounds 2 in the presence of AcCl lead again to the formation of nitriles.