Lithium dimethylamide, lithium diethylamide and lithium diisopropylami
de decompose, probably via an ap-lithium hydride elimination mechanism
, to give N-methylenemethylamine, N-ethylidene-ethylamine and N-isopro
pylideneisopropylamine, respectively. Lithium dibenzylamide and lithiu
m bis(trimethylsilyl)amide exhibited different behaviour. Lithium dibe
nzylamide decomposes via the rupture of carbon-nitrogen and carbon-car
bon bonds. to give toluene and benzene. and lithium bis(trimethylsilyl
)amide volatilizes without decomposition.