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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 ...
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.
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.
Triethyl phosphonoacetate is a reagent for organic synthesis used in the Horner-Wadsworth-Emmons reaction (HWE) or the Horner-Emmons modification. Triethyl phosphonoacetate can be added dropwise to sodium methoxide solution to prepare a phosphonate anion. It has an acidic proton that can easily be abstracted by a weak base.
Key in explaining the difference in reactivity is the electron density on the α-keto carbon atom. Perkow quinoline application Aryl enol phosphates formed in good yields (ca. 90%) in the Perkow reaction can be used as phosphorylating reagents, e.g. able to transform AMP into ATP .
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.
Diethyl phosphite can add across unsaturated groups via a hydrophosphonylation reaction. For example, it adds to aldehydes in a manner similar to the Abramov reaction: (C 2 H 5 O) 2 P(O)H + RCHO → (C 2 H 5 O) 2 P(O)CH(OH)R. It can also add to imines in the Pudovik reaction and Kabachnik–Fields reaction, [13] in both cases forming ...
Dimethylphosphite is an organophosphorus compound with the formula (CH 3 O) 2 P(O)H, known as dimethyl hydrogen phosphite (DMHP). Dimethylphosphite, is a minor tautomer of the phosphorus(V) derivative. It is a reagent for generating other organophosphorus compounds, exploiting the high reactivity of the P-H bond. The molecule is tetrahedral. It ...