Iminophosphorane

Iminophosphoranes (also known as phosphine imides, phosphinimide, phosphinimines, λ5-phosphazenes, acyclic phosphazenes) are a class of organophosphorus compounds and an acyclic subclass of phosphazenes with the general formula R3P=NR’. First reported by Staudinger and Meyer in 1919, these isoelectronic analogues of phosphine oxides and phosphonium ylides (also known as Wittig reagents) are most commonly synthesized via the Staudinger reaction or Kirsanov reaction, though alternative synthetic routes have also been developed.

The P=N bond is best described as a highly polarized single bond consistent with ylidic resonance structure R3P+=N-R', and the steric and electronic character may be tuned by varying the substituents on either the phosphorus or nitrogen. These properties allowing for interesting reactivity of iminophosphoranes as a Brønsted (super)base or coordinating ligand at the nitrogen, or for [2+2] cycloadditions with the P=N bond. As such, iminophosphoranes have found diverse applications as ligands for homogeneous catalysis (i.e. cross coupling, polymerization, etc.), superbasic or bifunctional organocatalysts, probes for chemical biology, and more.

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