Angewandte Chemie - International Edition
Angewandte Chemie - International Edition
4 years ago

Oxime Ether Radical Cations Stabilized by N-Heterocyclic Carbene

Kimoon Kim, Youngsuk Kim, Eunsung Lee
N-heterocyclic carbene nitric oxide (NHCNO) radicals, which can be regarded as iminoxyl radicals stabilized by NHCs, were found to react with a series of silyl and alkyl triflates to generate the corresponding oxime ether radical cations. The structures of the resulting oxime ether radical cations were determined by X-ray crystallography, along with EPR and computational analysis. In contrast, lutidinium triflate produced a 1:1 mixture of [NHCNO+][OTf-] and [NHCNHOH+][OTf-] upon the reaction with NHCNO. This study adds an important example of stable singlet carbenes stabilizing main group radicals due to their π-conjugating effect, the synthesis and structures of which have never been elucidated previously.

Publisher URL: http://onlinelibrary.wiley.com/resolve/doi

DOI: 10.1002/anie.201710530

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