Interaction of polyfluoroaromatic compounds with o-aminophenol. The Smiles rearrangement in the polyfluoroaromatic series |
| |
| Affiliation: | 1. Institute of Chemistry, Saint-Petersburg State University, Universitetsky pr. 26, 198504, Petrodvorets, Saint-Petersburg, Russia;2. St Petersburg National Research University of Information Technologies, Mechanics and Optics, Kronverkskiy pr. 49, 197101, Saint-Petersburg, Russia;3. Institute of Biochemistry and Molecular Medicine, NCCR TransCure, University of Bern, Bühlstrasse 28, 3012, Bern, Switzerland;4. Department of Chemistry, Saint Petersburg State Forest Technical University, Institutsky per. 5, Saint Petersburg, 194021, Russia;1. KU Leuven, Rega Institute for Medical Research, Medicinal Chemistry, Herestraat 49, 3000 Leuven, Belgium;2. KU Leuven, Rega Institute for Medical Research, Laboratory of Virology and Chemotherapy, Herestraat 49, 3000 Leuven, Belgium;1. School of Chemistry and Chemical Engineering, Jiangsu Normal University, Xuzhou 221116, PR China;2. Department of Chemistry, Xuzhou Medical University, Xuzhou 221004, PR China |
| |
| Abstract: | The reactions of polyfluoroaromatic compounds containing an electron-attracting substituent other than fluorine in the aromatic ring with o-aminophenol proceed at the amino or hydroxy group and lead to the corresponding hydroxydiarylamines (in neutral media) or aminodiaryl ethers (in alkaline media). The latter compounds, unlike 2,3,4,5,6-pentafluoro- 2'-aminodiphenyl ether, are transformed in dimethylformamide (DMFA) to isomeric polyfluoro-2-hydroxydiarylamines (the Smiles rearrangement). The increased electron-attracting capacity of substituent leads to the decreased activation energy and increased rearrangement rate constants. |
| |
| Keywords: | |
| 本文献已被 ScienceDirect 等数据库收录！ |
|
