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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.
Any −OH groups on the phosphates in these ester molecules may lose H + ions to form anions, again depending on the pH in a solution. In the biochemistry of living organisms, there are many kinds of (mono)phosphate, diphosphate, and triphosphate compounds (essentially esters ), many of which play a significant role in metabolism such as ...
The Michaelis–Arbuzov reaction is the chemical reaction of a trivalent phosphorus ester with an alkyl halide to form a pentavalent phosphorus species and another alkyl halide. Commonly, the phosphorus substrate is a phosphite ester (P(OR) 3) and the alkylating agent is an alkyl iodide. [11] The mechanism of the Michaelis–Arbuzov reaction
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.