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09-13-07_Magtrieve Lab Discussion

09-13-07_Magtrieve Lab Discussion - Solvent Free Magtrieve...

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Solvent Free Magtrieve Oxidation of Alcohols Norbert Wang Chem. 3BL Section 113 Reference: ROY J. GRITTER AND THOMAS J. WALLACE “Manganese Oxidation of Allylic Alcohols” January 16, 1959 - CONTRIBUTION FROM THE DEPARTMENT of CHEMISTRY of the UNIVERSITY of CONNECTICUT (from ACS archives) Discussion: In this 1959 report, it was found that manganese dioxide only oxidizes allylic hydroxyl groups, OH’s on the carbon next to a double bonded carbon. When performing oxidations with manganese catalysts, the solvent can be a major factor in the rate of reaction. This article discusses many of the solvent factors involved in producing an efficient oxidation. It was found that chloroform or CH 2 Cl 2 improved oxidation by 20% compared to the use of petroleum ether. When trying to oxidize benzyl alcohol, problems arose from using manganese. Another group of scientists reported that benzyl alcohol could not be oxidized using what they called “the dioxide of Rosenkranz, Sondheimer, and Mancera.” However the dioxide used in this article oxidized benzyl alcohol with 60% yield. One of the biggest conclusions from these series
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