期刊
CHEMISTRY-A EUROPEAN JOURNAL
卷 21, 期 23, 页码 8441-8446出版社
WILEY-V C H VERLAG GMBH
DOI: 10.1002/chem.201500740
关键词
carbenes; cyclic voltammetry; radicals; redox chemistry
资金
- German National Academic Foundation
- NSF [CHE-1359809]
- Direct For Mathematical & Physical Scien
- Division Of Chemistry [1359809] Funding Source: National Science Foundation
A stable cyclic (alkyl)(amino)carbene (CAAC) 1 inserts into the para-CF bond of pentafluoropyridine, and after fluoride abstraction, the iminium-pyridyl adduct [3](+) was isolated. A cyclic voltammetry study shows a reversible three-state redox system involving [3](+), [3], and [3](-). The CAAC-pyridyl radical [3], obtained by reduction of [3](+) with magnesium, has been spectroscopically and crystallographically characterized. In contrast to the lack of communication between the CAAC and the pyridine units in cation [3](+), the unpaired electron of [3] is delocalized over an extended system involving both heterocycles.
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