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Issue 6, 2013
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Electrochemical and spectroelectrochemical studies of C-benzodiazaborolyl-ortho-carboranes

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Abstract

Fifteen C-diazaborolyl-ortho-carboranes, 1-R′-2-R′′-1,2-C2B10H10, where R′ represents the groups 2-(1,3-Et2-1,3,2-N2BC6H4)-, 2-(1,3-Ph2-1,3,2-N2BC6H4)-, 2-(1,3-Ph2-5,6-Me2-1,3,2-N2BC6H2)-, 2-(1,3-iPr2-1,3,2-N2BC6H4)-, and 2-(1,3,2-N2BC6H6)- and where R′′ is H, Me, Ph, tBu or SiMe3, were synthesized. Cyclic voltammetry studies of the compounds showed irreversible oxidation waves which are caused by the oxidation of the heterocycle. Those C-diazaborolyl-ortho-carboranes with Ph, tBu and SiMe3 substituents at the adjacent C-atom of the cage displayed two one-electron reduction waves reflecting the formation of stable radical monoanions with unusual (2n + 3) skeletal electron counts. The geometries of these anions were determined by combinations of infrared, UV-visible spectroelectrochemical and computational studies. Additionally the structures of seven new C-diazaborolyl-ortho-carboranes and one new 2-bromo-1,3,2-benzodiazaborole were determined by X-ray crystallography and compared with previously obtained structures.

Graphical abstract: Electrochemical and spectroelectrochemical studies of C-benzodiazaborolyl-ortho-carboranes

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Publication details

The article was received on 08 Oct 2012, accepted on 13 Nov 2012 and first published on 13 Nov 2012


Article type: Paper
DOI: 10.1039/C2DT32378H
Citation: Dalton Trans., 2013,42, 2266-2281
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    Electrochemical and spectroelectrochemical studies of C-benzodiazaborolyl-ortho-carboranes

    L. Weber, J. Kahlert, L. Böhling, A. Brockhinke, H. Stammler, B. Neumann, R. A. Harder, P. J. Low and M. A. Fox, Dalton Trans., 2013, 42, 2266
    DOI: 10.1039/C2DT32378H

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