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A Crystalline Diazadiborinine Radical Cation and Its Boron-Centered Radical Reactivity
B. Wang, Y. Li, , R.D. Webster, R. Kinjo
Published in Wiley-VCH Verlag
PMID: 29683242
Volume: 57
Issue: 26
Pages: 7826 - 7829
One-electron oxidation of 1,4,2,5-diazadiborinine 1 has been studied. While the reaction of 1 a bearing phenyl groups on the B atoms with AgAl{OC(CF3)3}4 afforded a complex mixture, the same oxidation reaction with 1 b featuring bulky mesityl substituents on the B atoms rendered the corresponding cation radical 2 b as an isolable species. X-ray diffraction analysis, EPR spectroscopy, and DFT calculations of 2 b revealed the delocalization of the unpaired electron over the entire π-system of 2 b, as well as a large spin density (0.76 in total) on the two equivalent boron atoms. The chemical trapping reaction of 2 b with p-benzoquinone and triphenyltin hydride afforded the dicationic species 3 containing two newly formed B−O bonds and the monocationic product 2b-H containing a B−H bond, respectively, thus confirming the boron-centered radical reactivity of 2 b. © 2018 Wiley-VCH Verlag GmbH & Co. KGaA, Weinheim
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