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In organic chemistry
Organic chemistry is a subdiscipline within chemistry involving the scientific study of the structure, properties, and reactions of organic compounds and organic materials, i.e., matter in its various forms that contain carbon atoms.Clayden, J ...
, phosphonites are organophosphorus compound
Organophosphorus compounds are organic compounds containing phosphorus. They are used primarily in pest control as an alternative to chlorinated hydrocarbons that persist in the environment. Some organophosphorus compounds are highly effective i ...
s with the formula P(OR)2R. They are found in some pesticide
Pesticides are substances that are meant to control pests. This includes herbicide, insecticide, nematicide, molluscicide, piscicide, avicide, rodenticide, bactericide, insect repellent, animal repellent, microbicide, fungicide, and ...
s and are used as ligand
In coordination chemistry, a ligand is an ion or molecule (functional group) that binds to a central metal atom to form a coordination complex. The bonding with the metal generally involves formal donation of one or more of the ligand's elect ...
s.
Preparation
Although they are derivatives of phosphonous acid (RP(OH)2), they are not prepared from such precursors. Phosphonites are prepared byalcoholysis
In chemistry, solvolysis is a type of nucleophilic substitution (S1/S2) or elimination where the nucleophile is a solvent molecule. Characteristic of S1 reactions, solvolysis of a chiral reactant affords the racemate. Sometimes however, the ste ...
of organophosphinous chlorides. For example, treatment of dichlorophenylphosphine
Dichlorophenylphosphine is an organophosphorus compound with the formula C6H5PCl2. This colourless viscous liquid is commonly used in the synthesis of organophosphines.
Dichlorophenylphosphine is commercially available. It may be prepared by an ...
with methanol
Methanol (also called methyl alcohol and wood spirit, amongst other names) is an organic chemical and the simplest aliphatic alcohol, with the formula C H3 O H (a methyl group linked to a hydroxyl group, often abbreviated as MeOH). It is ...
and base gives dimethyl phenylphosphonite:
:Cl2PPh + 2 CH3OH → (CH3O)2PPh + 2 HCl
Reactions
Oxidation of phosphonites givesphosphonate
In organic chemistry, phosphonates or phosphonic acids are organophosphorus compounds containing groups (where R = alkyl, aryl, or just hydrogen). Phosphonic acids, typically handled as salts, are generally nonvolatile solids that are poorly ...
s:
:2 P(OR)2R + O2 → 2 OP(OR)2R
Phosphonites can function as ligand
In coordination chemistry, a ligand is an ion or molecule (functional group) that binds to a central metal atom to form a coordination complex. The bonding with the metal generally involves formal donation of one or more of the ligand's elect ...
s in homogeneous catalysis
In chemistry, homogeneous catalysis is catalysis by a soluble catalyst in a solution. Homogeneous catalysis refers to reactions where the catalyst is in the same phase as the reactants, principally in solution. In contrast, heterogeneous catalysi ...
.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.
References