Collect. Czech. Chem. Commun. 2007, 72, 1676-1688

Synthesis of Functional Derivatives of 7,8-Dicarba-nido-undecaborate Anion by Ring-Opening of Its Cyclic Oxonium Derivatives

Marina Yu. Stogniya,b, Ekaterina N. Abramovaa,c, Irina A. Lobanovaa, Igor B. Sivaeva,*, Vikentii I. Bragina, Pavel V. Petrovskiia, Viktoria N. Tsuprevaa, Olga V. Sorokinab and Vladimir I. Bregadzea

a A. N. Nesmeyanov Institute of Organoelement Compounds, Russian Academy of Sciences, Vavilov Str. 28, 119991 Moscow, Russia
b M. V. Lomonosov Moscow Academy for Fine Chemical Technology, Vernadskii Pr. 86, 117571 Moscow, Russia
c D. I. Mendeleev Russian Chemical Technological University, Miusskii Sq. 9, 125047 Moscow, Russia


A new approach to synthesis of functional derivatives of 7,8-dicarba-nido-undecaborate anion based on ring-opening of its cyclic oxonium derivatives [10-(CH2)4O-7,8-C2B9H11] and [10-O(CH2CH2)2O-7,8-C2B9H11] with various nucleophiles was developed. Both cyclic oxonium derivatives can be obtained as single isomers by reaction of the parent anion [7,8-C2B9H12]- with mercury(II) chloride in the corresponding solvents. Mechanism of formation of the cyclic oxonium derivatives of 7,8-dicarba-nido-undecaborate anion was proposed. A series of 7,8-dicarba-nido-undecaborate derivatives with terminal carboxylic and azide functions were prepared by the ring-opening reactions of the cyclic oxonium derivatives with substituted phenolate and azide ions, respectively.

Keywords: Carboranes; Functionalization; Oxonium derivatives; Carboxylic acids; Azides; Boron clusters; Boron hydrides.

References: 73 live references.