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Concept
Phosphonite
Summary
In organic chemistry, phosphonites are organophosphorus compounds with the formula P(OR)2R. They are found in some pesticides and are used as ligands.
Although they are derivatives of phosphonous acid (RP(OH)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
Oxidation of phosphonites gives phosphonates:
2 P(OR)2R + O2 → 2 OP(OR)2R
Phosphonites can function as ligands in homogeneous catalysis.
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Related concepts (4)
Organophosphorus chemistry
Organophosphorus chemistry is the scientific study of the synthesis and properties of organophosphorus compounds, which 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 insecticides, although some are extremely toxic to humans, including sarin and VX nerve agents. Phosphorus, like nitrogen, is in group 15 of the periodic table, and thus phosphorus compounds and nitrogen compounds have many similar properties.
Phosphonite
In organic chemistry, phosphonites are organophosphorus compounds with the formula P(OR)2R. They are found in some pesticides and are used as ligands. Although they are derivatives of phosphonous acid (RP(OH)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 Oxidation of phosphonites gives phosphonates: 2 P(OR)2R + O2 → 2 OP(OR)2R Phosphonites can function as ligands in homogeneous catalysis.
Phosphite ester
In organic chemistry, a phosphite ester or organophosphite usually refers to an organophosphorous compound with the formula P(OR)3. They can be considered as esters of an unobserved tautomer phosphorous acid, H3PO3, with the simplest example being trimethylphosphite, P(OCH3)3. Some phosphites can be considered esters of the dominant tautomer of phosphorous acid (HP(O)(OH)2). The simplest representative is dimethylphosphite with the formula HP(O)(OCH3)2. Both classes of phosphites are usually colorless liquids.