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The general structure of a phosphite ester showing the lone pairs on the P. 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, H 3 PO 3, with the simplest example being trimethylphosphite ...
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.
Phosphite esters with tertiary alkyl halide groups can undergo the reaction, which would be unexpected if only an S N 2 mechanism was operating. Further support for this S N 1 type mechanism comes from the use of the Arbuzov reaction in the synthesis of neopentyl halides, a class of compounds that are notoriously unreactive towards S N 2 reactions.
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.
Phosphites, sometimes called phosphite esters, have the general structure P(OR) 3 with oxidation state +3. Such species arise from the alcoholysis of phosphorus trichloride: PCl 3 + 3 ROH → P(OR) 3 + 3 HCl. The reaction is general, thus a vast number of such species are known.
An ester of carboxylic acid.R stands for any group (organic or inorganic) and R′ stands for organyl group.. In chemistry, an ester is a compound derived from an acid (organic or inorganic) in which the hydrogen atom (H) of at least one acidic hydroxyl group (−OH) of that acid is replaced by an organyl group (−R).
Triethyl phosphite (TEP) is an organophosphorus compound, specifically a phosphite ester, with the formula P(OCH 2 CH 3) 3, often abbreviated P(OEt) 3. It is a colorless, malodorous liquid. It is used as a ligand in organometallic chemistry and as a reagent in organic synthesis.
Trimethylolpropane phosphite, C 2 H 5 C(CH 2 O) 3 P, is a phosphite ester used as a ligand in organometallic chemistry. Trimethylolpropane phosphite is sometimes abbreviated to EtCage. It is a white solid that is soluble in organic solvents. It is also highly toxic. [1]