Starting with HOOC-CB11Me11- or CB11Me12- as the starting material, collision-induced dissociation has produced a series of methylated analogs of didehydro-closo-carbadodecaborane anions by sequential losses of up to 5 equiv of ethylene. These reactive intermediates are carborane analogues of doubly pyramidalized alkenes and, more distantly, arynes. Density functional theory calculations have been used to develop a proposal for the mechanism of the unusual formation of ethylene from the carborane methyl substituents.

Department of Chemistry University of Colorado Boulder Colorado 80309 0215 United States

Institute of Organic Chemistry and Biochemistry of the Czech Academy of Sciences Flemingovo nám 2 16610 Prague 6 Czech Republic

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Chlorinated Cubane-1,4-dicarboxylic Acids