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.
A. Basha and D. W. Brooks, J. Chem. Soc., Chem. Commun., 1987, 305 DOI: 10.1039/C39870000305
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