Oxidation of Primary Aliphatic and Aromatic Aldehydes with Difluoro(aryl)-λ^3-bromane
Oxidation of Primary Aliphatic and Aromatic Aldehydes with Difluoro(aryl)-λ^3-bromane
复制标题
二氟(芳基)-λ^3-溴烷氧化脂肪族和芳香族伯醛
DOI：
10.1021/ol202248x
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发表时间：
2011
期刊：
影响因子：
5.2
通讯作者：
and K. Miyamoto
中科院分区：
文献类型：
--
作者：
M. Ochiai;A. Yoshimura;Md. M. Hoque;T. Okubo;M. Saito;and K. Miyamoto
脂肪族伯醛与对三氟甲基苯基（二氟）-λ3-溴烷在二氯甲烷中于0 °C氧化，选择性地以良好的产率得到酰基氟，而芳香族醛在氯仿中于室温氧化，得到芳基二氟甲基醚。一个更大的迁移倾向的芳基相比，伯烷基基团在1，2-转移过程中从碳原子到一个缺电子的氧原子在溴烷（III）Criegee型中间体将导致这些差异的反应过程。
Oxidation of primary aliphatic aldehydes withp-trifluoromethylphenyl(difluoro)-λ3-bromane in dichloromethane at 0 °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.