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Phosphite esters are typically prepared by treating phosphorus trichloride with an alcohol. For alkyl alcohols the displaced chloride ion can attack the phosphite, causing dealkylation to give a dialkylphosphite and an organochlorine compound. [1] [2] The overall reaction is as follows: PCl 3 + 3 C 2 H 5 OH → (C 2 H 5 O) 2 P(O)H + 2 HCl + C 2 ...
The mechanism starts with an allylic sulfoxide 1 which undergoes a thermal 2,3-sigmatropic rearrangement to give a sulfenate ester 2. This can be cleaved using a thiophile, such as phosphite ester , which leaves the allylic alcohol 3 as the product.
General ester of phosphonous acid Not to be confused with phosphinite (formula P(OR)R 2 ). In organic chemistry , phosphonites are organophosphorus compounds with the formula P(OR) 2 R.
Organophosphorus chemistry is the scientific study of the synthesis and properties of organophosphorus compounds, which are organic compounds containing phosphorus. [1] They are used primarily in pest control as an alternative to chlorinated hydrocarbons that persist in the environment.
General ester of phosphonic acid; in fact, the phosphorus has a formal charge of +1, the oxygen above it has a formal charge of −1, and the bond between them is single. In organic chemistry, phosphonates or phosphonic acids are organophosphorus compounds containing C−PO(OR) 2 groups, where R is an organic group (alkyl, aryl).
Phosphonites are generally more reactive than phosphite esters. They react to produce phosphinates. Heating is also required for the reaction, but pyrolysis of the ester to an acid is a common side reaction. The poor availability of substituted phosphonites limits the usage of this class of reagent in the Arbuzov reaction.
Various specialised methods have been developed on the laboratory-scale for scientific investigations. These are rarely employed in bulk manufacturing. Examples include the Atherton-Todd reaction, which converts a dialkyl phosphite to a phosphoryl chloride. This can then react with an alcohol to give an organophosphate and HCl.
From the commercial perspective, the most important phosphite salt is basic lead phosphite. Many salts containing the phosphite ion have been investigated structurally, these include sodium phosphite pentahydrate (Na 2 HPO 3 ·5H 2 O). (NH 4) 2 HPO 3 ·H 2 O, CuHPO 3 ·H 2 O, SnHPO 3 and Al 2 (HPO 3) 3 ·4H 2 O. [4] The structure of HPO 2− 3 ...