INTERACTIONS OF ALKOXIDES .11. REACTIONS OF SUBSTITUTED N-LITHIUM AMIDES WITH HEAVIER ALKALI-METAL ALKOXIDES - NOVEL METHOD FOR THE PREPARATION OF N-SODIUM AND N-POTASSIUM DIALKYLAMIDES

Reactions of substituted N-lithium amides (RR′NLi) with heavier alkali metal alkoxides give rise to the corresponding heavier alkali metal amides. In this way, some N-sodium and N-potassium dialkylamides may be advantageously prepared in the pure state. These amides are much more reactive than lithium amides and readily metalate compounds containing CH bonds as weakly acidic as those in toluene. Metalations can also be carried out directly using a mixture of lithium amide and a heavier alkali metal alkoxide. The reactivity of N-sodium diisopropylamide was increased by the presence of sodium t-butoxide. A medium strength absorption was observed in the IR spectra of substituted alkali metal amides in the range 2800-2450 cm-1; this absorption is due to the stretching vibrations of the CH bond under the influence of anionic hyperconjugation". © 1979."