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Pure Appl. Chem., 2008, Vol. 80, No. 3, pp. 429-446

Chemistry of the three-dimensionally aromatic CB11 cage

Josef Michl

Department of Chemistry and Biochemistry, University of Colorado, Boulder, CO 80309-0215, USA

Abstract: After a brief introduction to the electronic structure of the three-dimensionally aromatic icosahedral closo-monocarbadodecaborate anion CB11H12-, some recent results for its permethylated version, CB11Me12- and three highly reactive electroneutral analogs are presented and discussed. These are the radical CB11Me12·, the boronium ylide CB11Me11 with a naked boron vertex, and the isomeric carbonium ylide with a naked carbon vertex. These ylides are probably better viewed as unusual types of singlet borylene and carbene, respectively.