lithium amide
lithamide

Lithium amides are very reactive compounds and can act as strong bases.

A model has been advanced that invokes an initial complex between the lithium amide base and epoxide.

Titration of lithium amide can be used to determine the amount of hydroxide in solution.

This white solid can be formed by a reaction between lithium amide and lithium hydride.

It reacts with hydrogen to make lithium hydride and lithium amide.

Alternatively, lithium amides may be prepared by the direct action of lithium on the corresponding amine.

Lithium amide can be made by adding lithium metal to liquid ammonia:

Treatment of this compound with lithium amide in ammonia affords optically pure inverted product.

In the Isler modification ethoxyacetylene is replaced by beta-chlorovinyl ether and lithium amide.

Deprotonation of tropinone with chiral lithium amides proceeded with modest enantioselectivity.

Key words: 1,3-proton transfer, chiral lithium amide, intramolecular, solvent-induced isomerization, stereospecific.

Key words: benzotriazole, lithium amides, aryl aldehydes.

For example, lithium dissolves in liquid ammonia to give a solution of lithium amide:

Most simple alkyllithium reagents, and common lithium amides are commercially available in a variety of solvents and concentrations.

Key words: chiral lithium amides, polymer-supported reagents, deprotonation, enolates, tropinone.

Keywords: 1,3-dioxan-5-ones, enantioselective deprotonation, chiral lithium amides.

Hirsch was also able to show the nucleophilic addition of amines by generating lithium amides, leading to amino-modified carbon nanotubes.

Care should be taken when HMPA is added to lithium amide reactions, as it is a known animal carcinogen.

An example of a lithium amide is lithium diisopropylamide (LDA), which is quite commonly used.

Instead, a racemic mixture of 3-tropinone is used with a chiral lithium amide base and additional ring expansion reactions in order to produce a ketone intermediate.

Thus lithium amide may also refer to lithium salts of amines e.g. LiNR.

This selectivity permitted us to probe the deprotonation of tropinone with lithium amides; it was concluded that the reaction involves predominantly the exo axial protons.

Dioxanones having two different alkyl groups at the 2-position were deprotonated enantioselectively by chiral lithium amide bases with enantiomeric excess (ee) of up to 70%.

Common lithium amides, e.g. lithium bis(trimethylsilyl)amide, and lithium diisopropylamide are also subject to aggregation.

Lithium amides adopt polymeric-ladder type structures in non-coordinating solvent in the solid state, and they generally exist as dimers in ethereal solvents.