In chemistry a phosphine imide (sometimes abbreviated to phosphinimide) also known as a iminophosphorane is a

functional group In organic chemistry, a functional group is a substituent or moiety in a molecule that causes the molecule's characteristic chemical reactions. The same functional group will undergo the same or similar chemical reactions regardless of the res ...

with the formula R₃P=NR. While structurally related to

phosphine oxide Phosphine oxides are phosphorus compounds with the formula OPX3. When X = alkyl or aryl, these are organophosphine oxides. Triphenylphosphine oxide is an example. An inorganic phosphine oxide is phosphoryl chloride (POCl3). Structure and bonding ...

its chemistry has more in common with phosphonium

ylide An ylide or ylid () is a neutral dipolar molecule containing a formally negatively charged atom (usually a carbanion) directly attached to a heteroatom with a formal positive charge (usually nitrogen, phosphorus or sulfur), and in which both ato ...

s. Anions of this group, with the structure R₃P=N⁻, are called

phosphinoimidate Phosphinoimidates, also known as phophinimides, are the anions derived from phosphine imides with the structure 3P=Nsup>− (R = alkyl or aryl). Phosphinimide ligands are used to for transition metal complexes that are highly active catalysts in ...

s and are used as ligands to form phosphinimide complexes which are highly active catalysts in some olefin polymerization reactions.

Synthesis

Phosphine imides can be isolated as intermediates in the

Staudinger reaction The Staudinger reaction is a chemical reaction of an organic azide with a phosphine or phosphite produces an iminophosphorane. The reaction was discovered by and named after Hermann Staudinger. The reaction follows this stoichiometry: :R3P + R ...

and have also been prepared by the action of

hydroxylamine-O-sulfonic acid Hydroxylamine-''O''-sulfonic acid (HOSA) is the inorganic compound with molecular formula H3NO4S that is formed by the sulfonation of hydroxylamine with oleum. It is a white, water-soluble and hygroscopic, solid, commonly represented by the cond ...

phosphine Phosphine ( IUPAC name: phosphane) is a colorless, flammable, highly toxic compound with the chemical formula , classed as a pnictogen hydride. Pure phosphine is odorless, but technical grade samples have a highly unpleasant odor like rotti ...

s, proceeding via a p-aminophosphonium salt. Phosphinimine

Reactions and applications

The functional group will readily hydrolyse to give a

and an

amine In chemistry, amines (, ) are compounds and functional groups that contain a basic nitrogen atom with a lone pair. Amines are formally derivatives of ammonia (), wherein one or more hydrogen atoms have been replaced by a substituent su ...

:R₃P=NR' + H₂O → R₃P=O + R'NH₂

Phosphinimide ligands Phosphinimide ligands, also known as phosphorane iminato ligands, are any of a class of organic compounds of the general formula NPR3−. The R groups represent organic substituents or, in rare cases, halides or NR2 groups. NPR3− is isoelectro ...

of the general formula NPR₃⁻ form

transition metal phosphinimide complexes Transition metal phosphinimide complexes are metal complexes that contain phosphinimide ligands of the general formula NPR3− (R = organic substituent). Several coordination modes have been observed, including terminal and various bridging geome ...

es. Some of these complexes are potential catalysts for the synthesis of

polyethylene Polyethylene or polythene (abbreviated PE; IUPAC name polyethene or poly(methylene)) is the most commonly produced plastic. It is a polymer, primarily used for packaging (plastic bags, plastic films, geomembranes and containers including ...

References

{{Functional groups Functional groups

Synthesis

Reactions and applications

See also

References