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

Only carbon,
hydrogen
and oxygen

Hydrocarbons	Allene Alkene (Allyl, Vinyl) Alkyl (Methyl, Ethyl, Propyl, Butyl, Pentyl) Alkyne Benzyl Carbene Cumulene Methylene bridge Methylene group Methine Phenyl

Other	Acetoxy Acetyl Acryloyl Acyl Aldehyde Alkoxy (Methoxy) Benzoyl Carbonyl Carboxyl Dioxirane Epoxide Ester Ether Ethylenedioxy Hydroxy Ketone Methylenedioxy Peroxide (Organic)

Only one
element
apart from
C, H, O

Nitrogen	Amine Azo compound Cyanate Hydrazone Imide Imine Isocyanate Isonitrile Nitrene Nitrile Nitro compound Nitroso compound Organic amide Oxime

Phosphorus	Phosphonate Phosphonous

Sulfur	Disulfide Sulfone Sulfonic acid Sulfoxide Thial Thioester Thioether Thioketone Thiol

Selenium	Selenol Selenonic acid Seleninic acid Selenenic acid

Tellurium	Tellurol

Other

See also chemical classification, chemical nomenclature (inorganic, organic)

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