Abstract
Oxidation of primary aliphatic aldehydes with p- trifluoromethylphenyl(difluoro)-λ 3-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.
Original language | English (US) |
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Pages (from-to) | 5568-5571 |
Number of pages | 4 |
Journal | Organic Letters |
Volume | 13 |
Issue number | 20 |
DOIs | |
State | Published - Oct 21 2011 |
Externally published | Yes |