sodium hydride

A well-known example is sodium hydride, which crystallizes in the NaCl motif.

The salt can be generated quantitatively by reaction with sodium hydride.

Deprotonation can be achieved with a variety of bases, typically sodium hydride or even sodium metal.

Since many substrates are not stable to sodium hydride, several procedures have been developed using milder bases.

Alkyl sulfoxides are susceptible to deprotonation by strong bases, such as sodium hydride.

Lastly, the molecule is turned into a cyclic molecule by reacting with sodium hydride.

It is used to generate dimethyloxosulfonium methylide by reaction with sodium hydride.

The salt is subsequently treated with sodium hydride in dichloromethane to form a ylide .

A derivative of this "inverse sodium hydride" arises in the presence of the base adamanzane.

In practice, most sodium hydride is dispensed as a dispersion in oil, which can be safely handled in air.