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Chemistry of icosahedral borane cluster dendritic precursors

Posted on:2010-05-14Degree:Ph.DType:Dissertation
University:The Ohio State UniversityCandidate:Kerechanin, Seth IFull Text:PDF
GTID:1441390002476787Subject:Chemistry
Abstract/Summary:
Aspects of chemistry of the previously known inner methyl sulfonium salts of [Me2SB12H11]- and 1,7-(Me 2S)2B12H10 have been studied. Reactions with nucleophiles like phthalimide and thiolate created methyl thioethers [MeSB12H11]2- and [1-(MeS),7-(Me 2S)B12H10]-. Alternately, [MeSB 12H11]2- and [1-(MeS),7-(Me2S)B 12H10]- can be synthesized by the reduction of the parent sulfonium salts by sodium or potassium in liquid ammonia. A variety of methyl thioethers have been synthesized and characterized through alkylation using a Michael addition-type reaction with alkyl halides.;In efforts to create dendrimer-like structures that have the ability to grow outward from a central core, multisubstituted benzene derivative compounds were synthesized using methylthio-icosahedral borane cage compounds as ligands linked by S(CH3)-CH2 units. This divergent dendrimer growth method was used to maximize the boron atom concentration while at the same time utilizing the dendrimer-type structure that could potentially lead to a variety of new and intriguing reactions.;All new compounds were characterized using advanced multinuclear NMR techniques and by mass-spectroscopy. The 11B {1H, 13C}, 1H, and 13C NMR spectra of the inner sulfonium salt, methyl thioethers, and thioether-sulfonium salts have been analyzed and certain trends were discovered. These trends allowed certain new reactions to be proposed and carried out. Interesting and new multisubstituted borane cage benzene derivatives were created and the idea of borane cage-based dendrimer structures was expanded.
Keywords/Search Tags:Borane, Methyl, New
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