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Issue 7, 2003
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Azacarbaborane chemistry. Butyl nitrite synthesis of the new eight-, nine- and ten-vertex azacarbaboranes exo- and endo-7-CH3-hypho-7,8-NCB6H11, nido-6,8,9-NC2B7H10, arachno-6,5,9-NC2B7H12 and arachno-6,5,10-C2NB7H12

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Abstract

The reaction between excess n-C4H9ONO and arachno-4,5-C2B7H13 (1) in diethyl ether at room temperature results in the formation of the first representatives of the arachno ten-vertex azadicarbaborane family, arachno-6,5,9-NC2B7H12 (2) and arachno-6,5,10-NC2B7H12 (3) in yields of 6 and 20%, respectively. The reaction also generates exo-8-CH3-hypho-7,8-NCB6H11 (4) (yield 5%) as a result of the extrusion of the CH2 group from the cluster of the starting dicarbaborane to generate a terminal methyl unit. The reaction between 8,9-μ-NH2-arachno-5,6-C2B8H11 (5) and NaH, followed by treatment with iodine and water, produced the unique endo isomer of 4, endo-8-CH3-hypho-7,8-NCB6H11 (6) (yield 22%). The reaction between n-C4H9ONO and nido-5,6-C2B8H12 (7) in hexane at reflux generates the first compound of the ten-vertex nido azadicarbaborane family, nido-6,8,9-C2NB7H10 (8), in 13% yield. The structures of all the compounds isolated are proposed on the basis of NMR spectroscopy, the geometries optimized at the RMP2(fc)/6-31G* level and their correctness was supported on the basis of GIAO-SCF NMR calculations.

Graphical abstract: Azacarbaborane chemistry. Butyl nitrite synthesis of the new eight-, nine- and ten-vertex azacarbaboranes exo- and endo-7-CH3-hypho-7,8-NCB6H11, nido-6,8,9-NC2B7H10, arachno-6,5,9-NC2B7H12 and arachno-6,5,10-C2NB7H12

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Publication details

The article was received on 03 Jan 2003, accepted on 20 Feb 2003 and first published on 04 Mar 2003


Article type: Paper
DOI: 10.1039/B300088E
Citation: Dalton Trans., 2003,0, 1326-1331

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    Azacarbaborane chemistry. Butyl nitrite synthesis of the new eight-, nine- and ten-vertex azacarbaboranes exo- and endo-7-CH3-hypho-7,8-NCB6H11, nido-6,8,9-NC2B7H10, arachno-6,5,9-NC2B7H12 and arachno-6,5,10-C2NB7H12

    T. Jelínek, B. Štíbr, J. D. Kennedy, D. Hnyk, M. Bühl and M. Hofmann, Dalton Trans., 2003, 0, 1326
    DOI: 10.1039/B300088E

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