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Issue 20, 2012
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Electrophilic substitution of the nido-dicarbaborate anion 7,8-nido-C2B9H12 with sulfenyl chlorides

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Abstract

Sulfenyl chlorides RSCl (R = p-C6H4OMe, Ph, p-C6H4NO2, CN or 2-C5H4N) react with 7,8-nido-C2B9H12 with asymmetric substitution on the pentagonal C2B3 face to give 9-RS-7,8-nido-C2B9H11 (R = p-C6H4OMe (3), Ph (4), p-C6H4NO2 (5), CN (6)) and the zwitterion 9-(S-2-C5H4NH)-7,8-nido-C2B9H11 (7), respectively, in high yield, while tBuSCl did not react and S2Cl2 led to decomposition. Further reaction of 5–7 with iodine gave the corresponding iodo derivatives NMe4 [9-I-11-RS-7,8-nido-C2B9H10] (R = p-C6H4NO2 (8), CN (9)) and the zwitterion 9-I-11-(S-2-C5H4NH)-7,8-nido-C2B9H11 (10), respectively. Compounds 3–10 were fully characterised by 1H, 11B, 11B{1H}, 13C{1H} spectroscopy, IR spectroscopy, mass spectrometry and elemental analysis, 3–7 also by 11B-11B{1H} COSY NMR spectroscopy and 8–10 by X-ray structure determination.

Graphical abstract: Electrophilic substitution of the nido-dicarbaborate anion 7,8-nido-C2B9H12− with sulfenyl chlorides

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Publication details

The article was received on 28 Dec 2011, accepted on 21 Mar 2012 and first published on 22 Mar 2012


Article type: Paper
DOI: 10.1039/C2DT12501C
Citation: Dalton Trans., 2012,41, 6155-6161
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    Electrophilic substitution of the nido-dicarbaborate anion 7,8-nido-C2B9H12 with sulfenyl chlorides

    R. Frank, T. Grell, M. Hiller and E. Hey-Hawkins, Dalton Trans., 2012, 41, 6155
    DOI: 10.1039/C2DT12501C

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