N,N-Disubstttuted Aminomethyllithium Compounds

Abstract

Five members of a novel class of heteroatom-substituted organometallic compounds, RR′NCH2Li, have been conveniently prepared by a transmetalation reaction between the appropriate (N,N-disubstttuted amino-methyl)tributyltin and n-butyllithium. The stabilities of these organolithium compounds varied with substitution at nitrogen. For example, in mixed tetrahydrofuran-hexane solvent, N,N-dimethylaminomethyllithium (1′) decomposed ca. 50% during 18 hr at 45°, while N-methyl-N-phenylaminomethyllithium decomposed completely within 4 hr at 25°. 1′ was found to be significantly less reactive than n-butyllithium as a metalating agent which thereby demonstrates that the N,N-dimethylamino substituent, relative to an alkyl group, has an overall stabilizing effect on a carbon-lithium bond. In addition to its obvious synthetic utility, 1′ proved useful as an intermediate for the conversion of benzophenone to (CH3)2NCH=C(C6H5)2and (C6H5)2CHCHO. © 1971, American Chemical Society. All rights reserved.