1412937-20-2Relevant academic research and scientific papers
Synthesis and characterization of B-heterocyclic π-radical and its reactivity as a boryl radical
Aramaki, Yoshitaka,Omiya, Hideki,Yamashita, Makoto,Nakabayashi, Koji,Ohkoshi, Shin-Ichi,Nozaki, Kyoko
supporting information, p. 19989 - 19992 (2013/02/23)
The first isolation and full characterization of the stable, persistent diazaboracyclic neutral radical 3 is reported. Reduction of base-stabilized difluororoborane 2 provided radical 3 as a neutral molecule having a planar sp2 boron atom attached to one fluorine and two nitrogen atoms. ESR spectroscopy and DFT calculations indicated that the unpaired electron is delocalized over the six-membered ring. Because of an electronic transition related to the singly occupied molecular orbital, 3 has a characteristic red color, as UV-vis spectroscopy showed an absorption maximum at 498 nm. Although DFT calculations suggested that radical 3 has relatively low spin density on the boron atom in comparison with the nitrogen and carbon atoms in the six-membered ring, 3 reacted as a base-stabilized boryl radical when treated with benzoquinone or benzoyl peroxide.
