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 |
|---|---|
| Pages (from-to) | 5568-5571 |
| Number of pages | 4 |
| Journal | Organic Letters |
| Volume | 13 |
| Issue number | 20 |
| DOIs | |
| Publication status | Published - 21 Oct 2011 |
| Externally published | Yes |
ASJC Scopus subject areas
- Biochemistry
- Physical and Theoretical Chemistry
- Organic Chemistry
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Ochiai, M., Yoshimura, A., Hoque, M. M., Okubo, T., Saito, M., & Miyamoto, K. (2011). Oxidation of primary aliphatic and aromatic aldehydes with difluoro(aryl)-λ 3-bromane. Organic Letters, 13(20), 5568-5571. https://doi.org/10.1021/ol202248x