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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 ...
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.
The Perkow reaction. In the related Michaelis–Arbuzov reaction the same reactants are known to form a beta-keto phosphonate which is an important reagent in the Horner–Wadsworth–Emmons reaction on the road to alkenes. The Perkow reaction, in this respect is considered a side-reaction.
The phosphite esters and tertiary phosphines also effect reduction: ROOH + PR 3 → P(OR) 3 + ROH. Cleavage to ketones and alcohols occurs in the base-catalyzed Kornblum–DeLaMare rearrangement, which involves the breaking of bonds within peroxides to form these products.
This reaction is a variant of the Michael addition: CH 2 =CHCO 2 R + 3 H 3 PO 3 → (HO) 2 P(O)CH 2 CH 2 CO 2 R. In the Hirao coupling dialkyl phosphites (which can also be viewed as di-esters of phosphonic acid: (O=PH(OR) 2) undergo a palladium-catalyzed coupling reaction with an aryl halide to form a phosphonate.
The Baeyer–Villiger oxidation is an organic reaction that forms an ester from a ketone or a lactone from a cyclic ketone, using peroxyacids or peroxides as the oxidant. [1] The reaction is named after Adolf von Baeyer and Victor Villiger who first reported the reaction in 1899.
This reaction is the basis of methods for analysis of organic peroxides. [5] Another way to evaluate the content of peracids and peroxides is the volumetric titration with alkoxides such as sodium ethoxide. [6] The phosphite esters and tertiary phosphines also effect reduction: ROOH + PR 3 → OPR 3 + ROH