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  3. Microwave-assisted metal-catalyzed reactions of halogenated carboranes
Title

Microwave-assisted metal-catalyzed reactions of halogenated carboranes

    Item Description
    Limited Access
    The author(s) chose to restrict access to this thesis to current Whitman students, faculty, and staff. Please log in to view it.
    Linked Agent
    Creator (cre): Rosenbaum, Aaron Joseph
    Advisor (adv): Juhasz, Mark
    Department (dpt): Whitman College. Chemistry Department
    Date
    December 7, 2012
    Graduation Year
    2012
    Abstract

    Palladium-catalyzed Rosenmund-von Braun conditions were applied to iodinated carboranes to prepare the first examples of cyano substituted derivatives of 1-carba-closo-dodecaborate( -1). Optimized microwave-assisted conditions with Pd(PPh₃)₂Cl₂ and copper (I) cyanide formed [12-CB₁₁H₁₁CN]⁻, [7,12-CB₁₁H₁₀(CN)₂]⁻, and [7,8,9,10,11,12-CB₁₁H₆(CN)₆]⁻ with great selectivity; products were purified and isolated as [Et₄N]⁺ salts in up to 81% yield. The compounds were characterized by NMR (¹¹B, ¹H, and ¹³C), LCMS, and IR. Single crystal X-ray diffraction revealed the structure of the [Et₄N][CB₁₁H₁₁CN] cage. Nitriles are known to undergo many organic reactions, and a preliminary investigation of hydrolysis of the cyano substituent revealed that the [12- CB₁₁H₁₁COOH]⁻ cage can be formed. This work also reports improved microwave assisted synthesis of halogenated and alkynylated carboranes along with attempted reactions of these compounds.

    Subject
    Carboranes -- 1-carba-closo-dodecaborate
    Chemical process -- Microwave irradiation
    Boron
    Halogenation
    Alkynes -- Alkynylation
    Science
    Academic theses
    Whitman College 2012 -- Dissertation collection -- Chemistry Department
    Genre
    Theses
    Extent
    132 pages
    Permanent URL
    http://works.whitman.edu/1187
    Rights
    http://rightsstatements.org/vocab/InC/1.0/
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