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Synfacts 2007(7): 0708-0708  
DOI: 10.1055/s-2007-968649
Synthesis of Materials and Unnatural Products
© Georg Thieme Verlag Stuttgart · New York

Stable Carborane Biradicals

Contributor(s): Timothy M. Swager, Eric L. Dane
L. Eriksson, K. Vyakaranam, J. Ludvik, J. Michl*
University of Colorado, Boulder, USA and J. Heyrovsk Institute of Physical Chemistry, Prague, Czech Republic
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Publication History

Publication Date:
22 June 2007 (online)

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Significance

Building on previously developed chemistry to functionalize the carba-closo-dodecaborate anion, Michl and co-workers report the synthesis of two neutral, isolable biradicals. In the key synthetic step, a Grob fragmentation converts 7 into carbocation 8, which can then react with 4 or 6 to form the dianion biradical precursors 9 and 10. Oxidation with PbO2 and extraction into pentane provides the neutral biradicals 11 and 12.