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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.
Mono- and di- esters are usually water soluble, particularity biomolecules. Tri-esters such as flame retardants and plasticisers have positive log Kow values ranging between 1.44 and 9.49, signifying hydrophobicity. [5] [23] [4] [24] Hydrophobic OPEs are more likely to be bioaccumulated and biomagnified in aquatic ecosystems. [3]
The Buchner–Curtius–Schlotterbeck reaction is the reaction of aldehydes or ketones with aliphatic diazoalkanes to form homologated ketones. [1] It was first described by Eduard Buchner and Theodor Curtius in 1885 [2] and later by Fritz Schlotterbeck in 1907. [3]
Phosphate esters have the general structure P(=O)(OR) 3 feature P(V). Such species are of technological importance as flame retardant agents, and plasticizers. Lacking a P−C bond, these compounds are in the technical sense not organophosphorus compounds but esters of phosphoric acid. Many derivatives are found in nature, such as ...
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.
General ester of phosphonic acid; in fact, the phosphorus has a formal charge of +1, the oxygen above it has a formal charge of −1, and the bond between them is single. In organic chemistry, phosphonates or phosphonic acids are organophosphorus compounds containing C−PO(OR) 2 groups, where R is an organic group (alkyl, aryl).
The zwitterionic intermediate rearranges to a cationic species while eliminating the halide. The cationic species then dealkylates through a second nucleophilic displacement in which the halide anion attacks one of the phosphite alkoxide substituents forming an enol phosphate. [1] Perkow reaction mechanism