Phosphonite
Organic compounds with the formula P(OR)2R
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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Organophosphorus
- PO3H2−
- P(O–)3
- P2O5·nH2O
- OP(O–)3
- –P(OH)2
- –P(O–)2
- –P(O)(O–)2
- –OP<
- free acid HOP(CF3)2
- HOP(O)<
- PO2H−
2 - –P<
- –P(O)<
- (–O)2PN<
- e.g. Nucleoside phosphoramidite
- (–O)2P(O)N<
- e.g. Phosphocreatine
- –OP(N<)2
- –OP(O)(N<)2
- P(N<)3
- e.g. P(NMe2)3
- OP(N<)3
- –NP(N<)3
- –P(O)(O–)N<
- –P(O)(N<)2
- >P(O)N<
- PSxO3−
4-x - (–O)3PS
- (-P)5