Phosphonite

Short description: Organic compounds with the formula P(OR)2R

General ester of phosphonous acid

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

In organic chemistry, 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 derivatives 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

1. ↑ D. E. C. Corbridge "Phosphorus: An Outline of its Chemistry, Biochemistry, and Technology" 5th Edition Elsevier: Amsterdam 1995. ISBN 0-444-89307-5.
2. ↑ IUPAC, Compendium of Chemical Terminology, 2nd ed. (the "Gold Book") (1997). Online corrected version:  (2006-) "phosphonous acids". doi:10.1351/goldbook.P04565
3. ↑ 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

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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

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Functional groups

| Only carbon,
hydrogen,
and oxygen|

| Hydrocarbons|

* Allene
* Alkene (Allyl group

|

Other|

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

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
* Selone

Tellurium|

* Tellurol
* Telluroketone

Other|

* Isothiocyanate
* Phosphoramide
* Sulfenyl chloride
* Sulfonamide
* Thiocyanate

See also chemical classification, chemical nomenclature ([[Chemistry:IUPAC nomenclature of inorganic, IUPAC nomenclature of organic chemistry|organic]])

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