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. 2015 Jun 1;21(23):8441-6.
doi: 10.1002/chem.201500740. Epub 2015 Apr 29.

Crystalline Cyclic (Alkyl)(amino)carbene-tetrafluoropyridyl Radical

Steffen Styra  1   2 , Mohand Melaimi  1 , Curtis E Moore  3 , Arnold L Rheingold  3 , Timo Augenstein  2 , Frank Breher  4 , Guy Bertrand  5
Affiliations

Crystalline Cyclic (Alkyl)(amino)carbene-tetrafluoropyridyl Radical

Steffen Styra et al. Chemistry. .

Abstract

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 π communication between the CAAC and the pyridine units in cation [3](+) , the unpaired electron of [3](⋅) is delocalized over an extended π system involving both heterocycles.

Keywords: carbenes; cyclic voltammetry; radicals; redox chemistry.

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