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Issue 11, 2008
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Synthesis and characterization of weakly coordinating anion salts of a new, stable carbocationic reagent, the dibenzosuberenyl (dibenzotropylium) ion

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Abstract

The new, bright red compounds [DBS][B(C6F5)4], [DBS][BCl(C6F5)3], [DBS][B(C6F5)3OH⋯H2O–B(C6F5)3] and [DBS][B(CH2CMe3)(C6F5)3] (DBS = C15H11, dibenzosuberenyl, dibenzotropylium, dibenzo[a,e]tropylium or dibenzo[a,d]cycloheptenocarbonium) have been synthesized and characterized spectroscopically and, except for [DBS][B(CH2CMe3)(C6F5)3], crystallographically. The crystal structures show that the DBS+ carbocation is planar and suggest pronounced delocalization of the positive charge over part of the seven-membered ring, in particular the CH carbon and the carbon atoms α and β to it. The electrophilic DBS+ carbocation activates alkene polymerization catalyst precursors of the type Cp′2ZrMe2, its efficacy being comparable to that of the well known but sterically more hindered trityl carbocation, Ph3C+. As with the Ph3C+ ion, DBS+ does not initiate carbocationic polymerization of isobutene in dichloromethane directly, but rather by reacting with trace amounts of water to generate protons.

Graphical abstract: Synthesis and characterization of weakly coordinating anion salts of a new, stable carbocationic reagent, the dibenzosuberenyl (dibenzotropylium) ion

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Publication details

The article was received on 26 Mar 2008, accepted on 08 May 2008 and first published on 18 Jul 2008


Article type: Paper
DOI: 10.1039/B804868A
Citation: New J. Chem., 2008,32, 1890-1898
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    Synthesis and characterization of weakly coordinating anion salts of a new, stable carbocationic reagent, the dibenzosuberenyl (dibenzotropylium) ion

    A. Cordoneanu, M. J. Drewitt, N. Bavarian and M. C. Baird, New J. Chem., 2008, 32, 1890
    DOI: 10.1039/B804868A

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