1496-94-2Relevant articles and documents
Stabilization of phosphobetaines that form in the reaction of trialkylphosphines with methoxyallene
Ovakimyan,Minasyan,Petrovskii,Indzkikyan
, p. 1154 - 1156 (1999)
Reactions of tripropyl- and tributylphosphines with methoxyallene were studied. In the case of tripropylphosphine, a mixture of tripropylphosphine oxide and tripropyl-1-formylethylidenephosphorane (the latter in equilibrium with its O-betaine) was obtained. The reaction with tributylphosphine yields, along with tributylphosphine oxide, two homologous ylides, namely, tributyl-1-formylethylidene- and tributyl-1-formylpropylidene-phosphoranes, which are also in equilibria with their O-betaines. A possible scheme of formation of these ylides is discussed.
Electrochemical oxidation of tertiary phosphines in the presence of camphene
Zagumennov,Sizova,Nikitin
experimental part, p. 1473 - 1482 (2009/12/04)
Anodic oxidation of tertiary phosphines (tripropyl-, tributyl-, and triphenylphosphine) in the presence of a bicyclic alkene (camphene) on a platinum and a glassy carbon electrodes was studied. For the first time the voltammetric characteristics of the process of camphene anodic oxidation were obtained. The electrochemical reactions with alkyl and aromatic phosphine were found to be dissimilar. The results of preparative electrooxidation of trialkylphosphines showed that in the course of electrolysis the tertiary phosphine cation-radicals generated on the anode enter into two concurrent reactions: (1) with the parent phosphine to form eventually trialkylphosphonium salts and trialkylphosphine oxides presumably as complex compounds and (2) with camphene to form trialkylcamphenylphosphonium salts and probably phosphonium salts with a monocyclic substituent. Preparative electrochemical oxidation of triphenylphosphine in the presence of camphene affords almost exclusively either triphenylphosphine oxide (in the experiment with platinum anode) or the triphenylphosphine oxide complex with perchloric acid (at the electrolysis on a glassy carbon anode).
Reactions of elemental phosphorus and phosphines with electrophiles in superbasic systems: XII. Synthesis of unsymmetrical tertiary phosphine oxides from red phosphorus and organyl halides
Gusarova,Shaikhudinova,Ivanova,Reutskaya,Albanov,Trofimov
, p. 718 - 720 (2007/10/03)
Alkyldibenzyl- and benzyldialkylphosphine oxides were prepared in one stage by direct phosphorylation of a mixture of alkyl bromides and benzyl chloride with red phosphorus under the conditions of phase-transfer catalysis (concentrated aqueous KOH solution-dioxane-benzyltriethylammonium chloride).
