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    Synthesis of cyclopropene derivatives and chemistry of fullerenes

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    Author
    Gesenberg, Christoph
    Date
    1997
    Degree
    Doctor of Philosophy
    Abstract
    New synthetic routes leading to 1-vinylcyclopropene and methylenecyclopropene were established making use of the Vacuum Gas-Solid Reaction (VGSR) technique. Both syntheses were planned in a way that allowed the use of solid fluoride as the dehalosilylation inducing reagent in the last step. The decomposition of methylenecyclopropene at temperatures above $-$75$\sp\circ$C was investigated and a dimer of methylenecyclopropene was proposed as the initial decomposition product. Fullerenes have been synthesized and separated using chromatographic techniques. Helium containing isomers of higher fullerenes were analyzed by $\sp3$He NMR spectroscopy and signals were assigned to isomers of C$\sb{76}$, C$\sb{78}$ and C$\sb{84}$. A novel C$\sb{60}$ derivative has been synthesized by the reaction of C$\sb{60}$ with cyclopropa (b) naphthalene and the product of the reaction with $\sp3$He@C$\sb{60}$ revealed the signal of the new compound in the $\sp3$He NMR. Fullerene hydrides $\sp3$He@C$\sb{60}$H$\sb{36}$ and $\sp3$He@C$\sb{60}$H$\sb{18}$ were synthesized by Birch reduction or reaction of $\sp3$He@C$\sb{60}$ with dihydroanthracene and the products were analyzed by $\sp3$He NMR. The spectra revealed one isomer for C$\sb{60}$H$\sb{18}$ and two isomers for C$\sb{60}$H$\sb{36}$. The most intense signal for C$\sb{60}$H$\sb{36}$ was assigned to the isomer with D$\sb{\rm 3d\sp\prime}$ symmetry based on the $\sp3$He NMR chemical shift value.
    Keyword
    Organic chemistry
    Citation
    Gesenberg, Christoph. "Synthesis of cyclopropene derivatives and chemistry of fullerenes." (1997) Diss., Rice University. https://hdl.handle.net/1911/19162.
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    • Rice University Electronic Theses and Dissertations [14030]

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    Home | FAQ | Contact Us | Privacy Notice | Accessibility Statement
    Managed by the Digital Scholarship Services at Fondren Library, Rice University
    Physical Address: 6100 Main Street, Houston, Texas 77005
    Mailing Address: MS-44, P.O.BOX 1892, Houston, Texas 77251-1892
    Site Map