Phosphonite

General ester of phosphonous acid

Not to be confused with phosphinite (formula P(OR)R₂).

Phosphonites are organophosphorus compounds with the formula P(OR)₂R. They are found in some pesticides and are used as ligands.^[1]

Preparation

Although they are derivivatives of phosphonous acid (RP(OH)₂),^[2] they are not prepared from such precursors. Phosphonites are prepared by alcoholysis of organophosphinous chlorides. For example, treatment of dichlorophenylphosphine with methanol and base gives dimethyl phenylphosphonite:

Cl₂PPh + 2 CH₃OH → (CH₃O)₂PPh + 2 HCl

Reactions

Oxidation of phosphonites gives phosphonates:

2 P(OR)₂R + O₂ → 2 OP(OR)₂R

Phosphonites can function as ligands in homogeneous catalysis.^[3]

References

↑ D. E. C. Corbridge "Phosphorus: An Outline of its Chemistry, Biochemistry, and Technology" 5th Edition Elsevier: Amsterdam 1995. ISBN 0-444-89307-5.
↑ IUPAC, Compendium of Chemical Terminology, 2nd ed. (the "Gold Book") (1997). Online corrected version: (2006–) "phosphonous acids".
↑ T. V. (Babu) Rajanbabu “Phosphinite and Phosphonite Ligands” in Phosphorus(III) Ligands in Homogeneous Catalysis: Design and Synthesis Paul C. J. Kamer and Piet W. N. M. van Leeuwen, Eds., John Wiley & Sons 2012. doi:10.1002/9781118299715.ch5

Organophosphorus

Only P-O bonds

P(III)	Phosphite/Organophosphite

P(V)	Phosphate/Organophosphate

With P-C bonds

One P-C bonds

P(III)	Phosphonite

P(V)	Phosphonate

Two P-C bonds

P(III)	Phosphinite

P(V)	Phosphinate

Three P-C bonds

P(III)	Phosphine

P(V)	Phosphine oxide

With P-N bonds

One P-N bond

P(III)	Phosphoramidite e.g. Nucleoside phosphoramidite

P(V)	Phosphoramidate e.g. Phosphocreatine

Two P-N bond

P(III)	Phosphorodiamidite

P(V)	Phosphorodiamidate e.g. Morpholino Cyclophosphamide

Three P-N bond

P(V)	Phosphoramide e.g. Hexamethylphosphoramide Metepa

With P-C and P-N bonds

One P-C bond and one P-N bond

P(V)	Phosphonamidate

One P-C bond and two P-N bond

P(V)	Phosphonamide

Two P-C bond and one P-N bond

P(V)	Phosphinamide

With P-S bonds

One P-S bond

P(III)	Phosphorothioite

P(V)	Phosphorothioate

Two P-S bond

P(III)	Phosphorodithioite

P(V)	Phosphorodithioate

Functional groups

Acetyl Acetoxy Acryloyl Acyl Alcohol Aldehyde Alkane Alkene Alkyne Alkoxy group Amide Amine Azo compound Benzene derivative Carbene Carbonyl Carboxylic acid Cyanate Disulfide Dioxirane Ester Ether Epoxide Haloalkane Hydrazone Hydroxyl Imide Imine Isocyanate Isonitrile Isothiocyanate Ketone Methyl Methylene bridge Methylene group Methine Nitrile Nitrene Nitro compound Nitroso compound Organophosphorus Oxime Peroxide Phosphonous and Phosphonic acid Pyridine derivative Selenol Selenonic acid Sulfenyl chloride Sulfone Sulfonic acid Sulfoxide Tellurol Thial Thiocyanate Thioester Thioether Thioketone Thiol Urea

See also Chemical classification

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