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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 ...
Solvents are often not used for this reaction, though there is precedent for the improvement of selectivity with its usage. [5] 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 ...
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.
When aliphatic alcohols are used the HCl by-product can react with the phosphate esters to give organochlorides and a lower ester. O=P(OR) 3 + HCl → O=P(OR) 2 OH + RCl. This reaction is usually undesirable and is exacerbated by high reaction temperatures. It can be inhibited by the use of a base or the removal of HCl through sparging.
The reaction mechanism of the Mitsunobu reaction is fairly complex. The identity of intermediates and the roles they play has been the subject of debate. Initially, the triphenyl phosphine (2) makes a nucleophilic attack upon diethyl azodicarboxylate (1) producing a betaine intermediate 3, which deprotonates the carboxylic acid (4) to form the ion pair 5.
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 ...
Alcohol oxidation is a collection of oxidation reactions in organic chemistry that convert alcohols to aldehydes, ketones, carboxylic acids, and esters. The reaction mainly applies to primary and secondary alcohols. Secondary alcohols form ketones, while primary alcohols form aldehydes or carboxylic acids. [1] A variety of oxidants can be used.
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.