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Trimethyl phosphite is an organophosphorus compound with the formula P(OCH 3) 3, often abbreviated P(OMe) 3.It is a colorless liquid with a highly pungent odor. It is the simplest phosphite ester and finds used as a ligand in organometallic chemistry and as a reagent in organic synthesis.
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 ...
Trimethyl phosphate is a mild methylating agent, useful for dimethylation of anilines and related heterocyclic compounds. [2] The method is complementary to the traditional Eschweiler-Clarke reaction in cases where formaldehyde engages in side reactions.
Phosphonic esters are prepared using the Michaelis–Arbuzov reaction. For example, methyl iodide catalyses the conversion of trimethylphosphite to the phosphonate ester dimethyl methylphosphonate: P(OMe) 3 → MePO(OMe) 2. These esters can be hydrolysed to the acid (Me = methyl): MePO(OMe) 2 + H 2 O → MePO(OH) 2 + 2 MeOH
Phosphate esters have the general structure P(=O)(OR) 3 feature P(V). Such species are of technological importance as flame retardant agents, and plasticizers. Lacking a P−C bond, these compounds are in the technical sense not organophosphorus compounds but esters of phosphoric acid. Many derivatives are found in nature, such as ...
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.
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.
Trimethylphosphine is a highly basic ligand that forms complexes with most metals. As a ligand, trimethylphosphine's Tolman cone angle is 118°. [7] This angle is an indication of the amount of steric protection that this ligand provides to the metal that to which it is bound.