Dissertation/Thesis Abstract

[3+2] Cycloaddition Reaction of Gem-Dicyanoepoxide and Electrophilic Reaction of Ethyl Atropate
by Jha, Jay Shankar, M.S., Southern Illinois University at Edwardsville, 2013, 71; 1545300
Abstract (Summary)

The epoxide-olefin [3+2] cycloaddition reaction is an important tool in synthesizing heterocyclic five member rings. Such cyclic compounds are well known for the formation of biologically active compounds. In this experiment, we developed a method for a [3+2] cycloaddition reaction between gem-dicyano phenyl epoxide and diethyl (E)-2-fluoromaleate to synthesize 2, 2-dicyano-3, 4-diethoxycarbonyl-4-fluoro-5-phenylfuran. The yield of the product was 55.56 %.

Fluorine is small in size and is the most electronegative element. These properties of fluorine make its incorporation into drugs easy and also increase the efficacy and selectivity of the drugs. Atropic acid has wide applications as an antagonist. The non-fluorinated atropic acid derivative binds to glycine binding sites, which help in the treatment of a number of disease states. Moreover, its derivatives are used in the preservation of beverages, pests control agents and fungicides. Considering the above facts, fluorination of ethyl atropate using XeF2 via an electrophilic addition reaction in the presence of compounds like I2, Se2Ph 2 and S2Ph2 was performed. The percentage yield of addition products were fairly high, ranging from 63 % to 67 %.

Indexing (document details)
Advisor: Patrick, Timothy B.
Commitee: Dixon, Robert, Lu, Yun
School: Southern Illinois University at Edwardsville
Department: Chemistry
School Location: United States -- Illinois
Source: MAI 52/02M(E), Masters Abstracts International
Source Type: DISSERTATION
Subjects: Organic chemistry
Keywords: Atropate, Cycloaddition, Furan
Publication Number: 1545300
ISBN: 9781303391422
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