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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.
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 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.
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.
In the case of trimethylphosphine, triphenyl phosphite is used in place of the highly electrophilic PCl 3: [6] 3 CH 3 MgBr + P(OC 6 H 5) 3 → P(CH 3) 3 + 3 C 6 H 5 OMgBr. Slightly more elaborate methods are employed for the preparation of unsymmetrical tertiary phosphines, with the formula R 2 R'P. The use of organophosphorus-based ...
[4] [5] The reaction has since been extended to the synthesis of β-keto esters from the condensation between aldehydes and diazo esters. [6] The general reaction scheme is as follows: General Scheme for Buchner Reaction. The reaction yields two possible carbonyl compounds (I and II) along with an epoxide (III). The ratio of the products is ...