Boron Trifluoride Promoted Addition of Organolithiums to Oxime Ethers. A Facile Synthesis of Substituted Hydroxylamines

Abstract

In the presence of diethyl ether-boron trifluoride complex, organolithiums add to the carbon-nitrogen double bond of oxime O-ethers to give the corresponding O-alkylhydroxylamines. On acid treatment, O-methoxymethylhydroxylamines obtained were easily transformed to N-monosubstituted hydroxylamine hydrochlorides.