Reaction of O-benzyl-N-methylenehydroxylamine with organolithium compounds, a CH2+–NH+ synthetic equivalent

Abstract

Lithium carbanions add sequentially to O-benzyl-N-methylenehydroxylamine (1), first at eh electrophioic carbon and subsequently, at higher temperature, on the nitrogen with concomitant loss of the benzyloxy group, resulting in a CH₂⁺–NH⁺ synthetic equivalent, the amines (4) being produced.