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Synthesis of Substituted Oxabenzonorbornadienes and their Reactions

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Title: Synthesis of Substituted Oxabenzonorbornadienes and their Reactions
Author: Haner, Jamie
Department: Department of Chemistry
Program: Chemistry
Advisor: Tam, William
Abstract: This thesis describes investigations on the topic of the versatile organic scaffold, 7-oxabenzonorbornadiene. The synthesis of 2-alkyl substituted furans via iron-catalyzed coupling of Grignard reagents and 2-bromofuran was optimized and various groups were coupled to furan. Primary and secondary alkyl groups were coupled with moderate to low yields of up to 56% were obtained. Furan-benzyne cycloaddition led to the formation of the corresponding C-1 substituted oxabenzonorbornadiene in yields of up to 70%. This methodology allows for access to uniquely substituted, strained bicyclic alkenes for further studies. The second part of this thesis describes the cyclopropanation of oxabenzonorbornadiene and the subsequent discovery of several reactions of the cyclopropane. The conditions for cyclopropanation were optimized, obtaining this product in yields of up to 98%. Treatment of this cyclopropane under electrophilic conditions led to the formation of (2-naphthyl)methanes in up to 98% yields, whereas treatment under nucleophilic conditions led to the formation of dihydronaphthols in up to >99% yield. The optimization of these reactions and mechanistic studies are described.
Date: 2011-08
Rights: Attribution-NonCommercial-NoDerivs 2.5 Canada

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Attribution-NonCommercial-NoDerivs 2.5 Canada Except where otherwise noted, this item's license is described as Attribution-NonCommercial-NoDerivs 2.5 Canada