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CHEMISTRY OF ICOSAHEDRAL BORANE CLUSTER DENDRITIC PRECURSORS

Kerechanin, Seth Ivan
http://rave.ohiolink.edu/etdc/view?acc_num=osu1253561259

Abstract Details

2009, Doctor of Philosophy, Ohio State University, Chemistry.
Aspects of chemistry of the previously known inner methyl sulfonium salts of [Me2SB12H11]- and 1,7-(Me2S)2B12H10 have been studied. Reactions with nucleophiles like phthalimide and thiolate created methyl thioethers [MeSB12H11]2- and [1-(MeS),7-(Me2S)B12H10]-. Alternately, [MeSB12H11]2- and [1-(MeS),7-(Me2S)B12H10]- 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.
Sheldon Shore (Advisor)
Claudia Turro (Committee Member)
Pat Woodward (Committee Member)
Timothy Schroeder (Committee Member)
155 p.
Chemistry
icosahedral borane dendrimer

Recommended Citations

Citations

  • Kerechanin, S. I. (2009). CHEMISTRY OF ICOSAHEDRAL BORANE CLUSTER DENDRITIC PRECURSORS [Doctoral dissertation, Ohio State University]. OhioLINK Electronic Theses and Dissertations Center. http://rave.ohiolink.edu/etdc/view?acc_num=osu1253561259

    APA Style (7th edition)

  • Kerechanin, Seth. CHEMISTRY OF ICOSAHEDRAL BORANE CLUSTER DENDRITIC PRECURSORS. 2009. Ohio State University, Doctoral dissertation. OhioLINK Electronic Theses and Dissertations Center, http://rave.ohiolink.edu/etdc/view?acc_num=osu1253561259.

    MLA Style (8th edition)

  • Kerechanin, Seth. "CHEMISTRY OF ICOSAHEDRAL BORANE CLUSTER DENDRITIC PRECURSORS." Doctoral dissertation, Ohio State University, 2009. http://rave.ohiolink.edu/etdc/view?acc_num=osu1253561259

    Chicago Manual of Style (17th edition)

osu1253561259
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© 2009, all rights reserved.
This open access ETD is published by The Ohio State University and OhioLINK.