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Facile Preparation of 4-Substituted Quinazoline Derivatives
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Substitution Reactions on Iodine and Bromine: Mechanisms for Facile Halogenations of Heterocycles
Leah L Donham1, Scott Gronert1,2
1Department of Chemistry , Virginia Commonwealth University , 1001 W Main Street , Richmond , Virginia 23284 , United States.
Abstract:
Gas-phase techniques were used to examine the halogenation of deprotonated heterocycles by perfluoroaryl and perfluoroalkyl halides. The results indicate that SN2@Br and SN2@I reactions can be very facile and are effective means of halogenating heterocycles. 2-Iodoheptafluoropropane is exceptionally selective for SN2@I reactions with yields upward of 90%. The results also provide evidence counter to the recent suggestion that t-butoxide-induced halogenations of heterocycles proceed via a radical mechanism.
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Halogens
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Reaction Mechanisms
For instance, the decomposition of ozone appears to follow a mechanism with two steps: