Dissertation/Thesis Abstract

1, 3-Dipolar Reaction of gem-Dicyanoepoxide with a Fluoro-Olefin
by Cherukuri, HimaBindu, M.S., Southern Illinois University at Edwardsville, 2014, 89; 1566668
Abstract (Summary)

Cycloaddition reactions are one of the greatest types of pericyclic reactions that involve in the formation of a cyclic product by the reaction of two or more unsaturated molecules resulting the reduction of multiplicity of bonds. The Huisgen 1, 3 -dipolar cycloaddition results in the formation of a five membered hetero ring by the reaction of a dipolarophile with a 1, 3-dipolar compound. These heterocycles show unique biological properties. We investigated a synthetic pathway for the [3+2] cycloaddition reaction between gem-dicyano phenyl epoxide with diethyl (E)-2-fluoromaleate to synthesize 2, 2-dicyano-3, 4-diethoxycarbonyl-4-fluoro-5-phenylfuran. The high electronegativity, small atomic radius and low polarizability of the C-F bond are the unique properties of the fluorine atom that contribute to make more fluoro-organic compounds. The replacement of a C-H bond or C-O bond with a C-F bond often brings out particular properties like increased metabolic stability, higher binding to target molecules, and enhanced hydrophobicity and membrane potential

Indexing (document details)
Advisor: Shaw, Michael
Commitee: Khazaeli, Sadegh, Shaw, Michael, Voss, Eric J.
School: Southern Illinois University at Edwardsville
Department: Chemistry
School Location: United States -- Illinois
Source: MAI 53/06M(E), Masters Abstracts International
Subjects: Inorganic chemistry, Organic chemistry, Nuclear chemistry
Publication Number: 1566668
ISBN: 978-1-321-25155-5
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