Journal
ANGEWANDTE CHEMIE-INTERNATIONAL EDITION
Volume 57, Issue 1, Pages 262-265Publisher
WILEY-V C H VERLAG GMBH
DOI: 10.1002/anie.201710530
Keywords
carbenes; iminoxyl radicals; nucleophilic addition; structure determination; X-ray diffraction
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Funding
- Institute for Basic Science (IBS) [IBS-R007-D1]
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N-heterocyclic carbene (NHC) 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 for stabilizing main-group radicals because of their pi-conjugating effect, the synthesis and structures of which have not been reported previously.
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