Phosphonite

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

General ester of phosphonous acid

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

↑ 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". doi:10.1351/goldbook.P04565
↑ 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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[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