Journal of the American Chemical Society
Journal of the American Chemical Society
5 years ago

Generation and Structure of Unique Boriranyl Radicals

Generation and Structure of Unique Boriranyl Radicals
Dennis P. Curran, Timothy R. McFadden, John C. Walton
Three-member ring boracyclopropanes (boriranes) with N-heterocyclic carbene substituents were prepared by a recently discovered route. H atoms were selectively abstracted from the boron atoms by t-butoxyl radicals and this enabled boriranyl radicals to be detected and characterized by EPR spectroscopy for the first time. Their EPR parameters indicated they had planar π-character. From competition experiments, the rate constant for H atom abstraction was determined and found to be about 2 orders of magnitude less than for NHC-boranes. The B–H BDE of an NHC-borirane was estimated to be about 95 kcal mol–1.

Publisher URL: http://dx.doi.org/10.1021/jacs.7b10788

DOI: 10.1021/jacs.7b10788

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