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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.
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.
Chemicals which can be used as weapons, or used in their manufacture, but which have no, or almost no, legitimate applications as well are listed in Schedule 1, whilst Schedule 2 is used for chemicals which have legitimate small-scale applications. The use of Schedule 1, 2, or 3 chemicals as weapons is banned by the Convention.
Dimethyl methylphosphonate can be prepared from trimethyl phosphite and a halomethane (e.g. iodomethane) via the Michaelis–Arbuzov reaction. [2]Dimethyl methylphosphonate is a schedule 2 chemical as it may be used in the production of chemical weapons.
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.
The second step involves treatment with trimethyl phosphite, which attacks the sulfur atom, producing S=P(OMe) 3 (driven by the formation of a strong P=S double bond) and leaving a carbene. [6] This carbene collapses with loss of carbon dioxide to give the olefin. Proposed Mechanism of the Corey-Winter Olefination