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Syntheses and structures of benzo-bis(1,3,2-diazaboroles) and acenaphtho-1,3,2-diazaboroles

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Abstract

Colorless crystalline 2,6-dibromo-4,8-dimethyl-1,3,5,7-tetraphenylbenzobis(diazaborole) 4 resulted from the cyclocondensation of 3,6-dimethyl-1,2,4,5-tetraphenylaminobenzene 3d with two equivalents of boron tribromide in the presence of calcium hydride. Synthesis of the dark-red crystalline 2-bromo-N,N′-bis(diisopropylphenyl)acenaphtho-1,3,2-diazaborole 7 was effected by the cyclocondensation of 1,2-bis(N-2′,6′-diisopropylphenylimino)acenaphthene (5) and boron tribromide with subsequent sodium amalgam reduction of the initially formed burgundy red diazaborolium salt 6. Compounds 4, 6 and 7 are characterised by elemental analyses, 1H, 11B and 13C NMR spectroscopy, as well as by single X-ray diffraction studies. The electronic structures of 4, 6 and 7 are subject to DFT calculations.

Graphical abstract: Syntheses and structures of benzo-bis(1,3,2-diazaboroles) and acenaphtho-1,3,2-diazaboroles

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Publication details

The article was received on 26 Sep 2019, accepted on 25 Oct 2019 and first published on 25 Oct 2019


Article type: Paper
DOI: 10.1039/C9DT03818C
Dalton Trans., 2019, Advance Article

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    Syntheses and structures of benzo-bis(1,3,2-diazaboroles) and acenaphtho-1,3,2-diazaboroles

    L. Weber, D. Eickhoff, A. Chrostowska, A. Dargelos, C. Darrigan, H. Stammler and B. Neumann, Dalton Trans., 2019, Advance Article , DOI: 10.1039/C9DT03818C

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