565-69-5Relevant articles and documents
Conversion of Propanal to Pentan-3-one using Lanthanide Oxides
Claridge, John B.,Green, Malcolm L. H.,Tsang, Shik Chi,York, Andrew P. E.
, p. 1089 - 1094 (1993)
The heterogeneous reaction between propanal vapour and rare-earth-metal oxides gives as major products pentan-3-one and carbon dioxide.Residence time investigations indicate that pentan-3-one and carbon dioxide are primary products.Deactivation and high-resolution electron microscopy studies support the hypothesis that surface participates in the reaction, and high oxygen mobilities in the oxide may allow defects to spread within the oxide.The carbon dioxide produced in the reaction poisons the lanthanum oxide leading to the faster deactivation and temperature-programmed desorption indicates the presence of a surface intermediate which decomposes to pentan-3-one and carbon dioxide.A mechanism is proposed in which the formation of pentan-3-one proceeds via surface-bound carboxylate species.Preliminary studies show that catalytic production of pentan-3-one can potentially be sustained by co-feeding water with propanal to the rare-earth-metal oxides.
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Munk
, p. 664 (1905)
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Selective Catalytic Hydration of Alkynes in the Presence of Au-Cavitands: A Study in Structure–Activity Relationships
Inoue, Mami,Ugawa, Katto,Maruyama, Tomoyuki,Iwasawa, Tetsuo
, p. 5304 - 5311 (2018/09/12)
The effects of the catalytic cavities in gold-functionalized cavitands in the hydration of internal alkynes have been studied. Variations on cavitand structures revealed the importance of two features that were studied: (1) flanking aromatic rings, and (2) an adjacent P=O moiety. The di-quinoxaline-spanned resorcin[4]arene system provides a well-defined compartment, in which a cationic Au ion activates an internal alkyne for conversion into a ketone by delivery of water that has also been activated, this time by a P=O moiety. We synthesized four variations on our parent cavitand. Variations of the cavitand walls include replacement of quinoxaline components with pyrazine or methylene units. Variation of the P=O center was accomplished with methylene or quinoxaline moieties. All variants displayed lower catalytic activity or selectivity, allowing us to confirm the significance both of an internal cavity and of an activation site for water.
Regioselective Isomerization of 2,3-Disubstituted Epoxides to Ketones: An Alternative to the Wacker Oxidation of Internal Alkenes
Lamb, Jessica R.,Mulzer, Michael,Lapointe, Anne M.,Coates, Geoffrey W.
, p. 15049 - 15054 (2015/12/08)
We report an alternative pathway to the Wacker oxidation of internal olefins involving epoxidation of trans-alkenes followed by a mild and highly regioselective isomerization to give the major ketone isomers in 66-98% yield. Preliminary kinetics and isotope labeling studies suggest epoxide ring opening as the turnover limiting step in our proposed mechanism. A similar catalytic system was applied to the kinetic resolution of select trans-epoxides to give synthetically useful selectivity factors of 17-23 for benzyl-substituted substrates.
