Iminophosphorane

Iminophosphorane (or, more correctly, phosphanimine) is a kind of organophosphorus compound with the formula R3PNR'.

Like the corresponding phosphine oxides and Wittig reagents, phosphanimines are ylides.

[1] Aza-ylides can be obtained via the reaction of a tertiary phosphine and an organic azide with the loss of dinitrogen.

The parent phosphanimine has the formula H3P=NH (registry number 25682-80-8) remains only of theoretical interest.

A prototype is the phenyl imide derivative of triphenylphosphine, a white, lipophilic solid.

Tetraphenylphosphanimine , an example of a phosphanimine.
Resonance structures for iminophosphoranes.
Mechanism of iminophosphorane formation