6652-27-3Relevant academic research and scientific papers
Iron(III)-catalyzed nucleophilic substitution of the hydroxy group in benzoin by alcohols
Mirzaei, Anvar,Biswas, Srijit,Samec, Joseph S. M.
experimental part, p. 1213 - 1218 (2012/06/04)
The etherification reaction between benzoin derivatives and alcohols catalyzed by iron(III) proceeds in moderate to good yields. Other metal complexes showed either low reactivity or low chemoselectivity where oxidation of benzoin to benzil was a competing reaction. The iron source operated as a catalyst where 5 mol% of iron(III) generate the 2-alkoxy-1,2-diphenylethan-1-one in 50% yield. With an optimum of 25 mol% of catalyst, the desired ether was obtained in 85% yield. The etherification of benzoin and an alcohol proceed to generate the desired product in polar solvents such as 1,2-dichloroethane, whereas less polar solvents promote the competing oxidation to generate the benzil; polar coordinating solvents such as tetrahydrofuran inhibited the reaction. The efficiency of the reaction is found to be dependent on nucleophile where an optimum of 30 equivalents of alcohol was observed. With electron-donating substituents on the aromatic ring, the etherification was followed by oxidation to generate the benzil. Moderate yields of etherification product were obtained by monitoring the reaction progress with electron-rich substrates and quenching the reaction after two hours. Georg Thieme Verlag Stuttgart New York.
Oxidation of Alkynes by Hydrogen Peroxide Catalyzed by Methylrhenium Trioxide
Zhu, Zuolin,Espenson, James H.
, p. 7728 - 7732 (2007/10/03)
The oxidation of alkynes with hydrogen peroxide is catalyzed by methylrhenium tioxide.The reactions can be rationalized by postulating that an oxirene intermediate is formed between a rhenium peroxide and the alkyne.Internal alkynes yield α-diketones and carboxylic acids, the latter from the complete cleavage of the triple bonds.Rearrangement products were observed only for aliphatic alkynes.Terminal alkynes gave carboxylic acids and their derivatives and α-keto acids as the major products, but their yields varied with the solvent used.
Bisbenzoin ethers and method of producing benzoin ethers
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, (2008/06/13)
New bisbenzoin ethers are produced. The method of producing the bisbenzoin ethers comprises the reaction of an alkyl glycol with benzoin utilizing phosphorous oxychloride as the catalyst with hydrogen chloride as acid reacting agent. The use of phosphorous oxychloride as catalyst with hydrogen chloride improves the production of benzoin ethers in general by the reaction of benzoin with the selected alcohol.
