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A Crystalline Diazadiborinine Radical Cation and Its Boron-Centered Radical Reactivity

A Crystalline Diazadiborinine Radical Cation and Its Boron-Centered Radical Reactivity

Baolin Wang, Yongxin Li, Rakesh Ganguly, Richard D Webster, Rei Kinjo

Angew Chem Int Ed Engl. 2018 Jun 25;57(26):7826-7829.

PMID: 29683242

Abstract:

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.

Chemicals Related in the Paper:

Catalog Number	Product Name	Structure	CAS Number	Price
AP892206	Triphenyltin hydride		892-20-6	Price

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