Phosphine oxides

Some discussions invoked a role for phosphorus-centered d-orbitals in bonding, but this analysis is not supported by computational analyses.

In order to suppress this reaction, air-free techniques are often employed when handling say, trimethylphosphine.

Regeneration of the tertiary phosphine requires cheap oxophilic reagents, which are usually silicon-based.

Industrial routes use phosgene or equivalent reagents, which produce chlorotriphenylphosphonium chloride, which is separately reduced.

[11] For chiral phosphine oxides, deoxygenation can proceed with retention or inversion of configuration.

Classically, inversion is favored by a combination of trichlorosilane and triethylamine, whereas in the absence of the Lewis base, the reaction proceeds with retention.

[10] Phosphoric acids ((RO)2PO2H) catalyze the deoxygenation of phosphine oxides by hydrosilanes.