Oxidation of Primary Aliphatic and Aromatic Aldehydes with Difluoro(aryl)-位3-bromane

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• 作者：Masahito Ochiai ; Akira Yoshimura ; Md. Mahbubul Hoque ; Takuji Okubo ; Motomichi Saito ; Kazunori Miyamoto
• 刊名：Organic Letters
• 出版年：2011
• 出版时间：October 21, 2011
• 年：2011
• 卷：13
• 期：20
• 页码：5568-5571
• 全文大小：711K
• 年卷期：v.13,no.20(October 21, 2011)
• ISSN：1523-7052

文摘

Oxidation of primary aliphatic aldehydes with p-trifluoromethylphenyl(difluoro)-位³-bromane in dichloromethane at 0 掳C afforded acid fluorides selectively in good yields, while that of aromatic aldehydes in chloroform at room temperature produced aryl difluoromethyl ethers. A larger migratory aptitude of aryl groups compared to primary alkyl groups during a 1,2-shift from carbon to an electron-deficient oxygen atom in bromane(III) Criegee-type intermediates will result in these differences in the reaction courses.