Generation and structure of unique boriranyl radicals
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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.
Walton , J C , McFadden , T R & Curran , D P 2017 , ' Generation and structure of unique boriranyl radicals ' Journal of the American Chemical Society , vol. 139 , no. 46 , pp. 16514-16517 . https://doi.org/10.1021/jacs.7b10788
Journal of the American Chemical Society
Copyright © 2017 American Chemical Society. This work has been made available online in accordance with the publisher’s policies. This is the author created, accepted version manuscript following peer review and may differ slightly from the final published version. The final published version of this work is available at https://doi.org/10.1021/jacs.7b10788
DescriptionJ.C.W. thanks EaStCHEM for financial support. T.R.M. and D.P.C. thank the US National Science Foundation for grant CHE-1660927.
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