Isobenzofuran-aryne cycloadducts: formation and regioselective conversion to anthrones and substituted polycyclic aromatics

J Netka, SL Crump, B Rickborn

Index: Netka, Jill; Crump, Stephen L.; Rickborn, Bruce Journal of Organic Chemistry, 1986 , vol. 51, # 8 p. 1189 - 1199

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Citation Number: 34

Abstract

Several substituted anthracenes, benz [a] anthracenes, dibenz [a, c] anthracene, and more complex ring system derivatives are formed by the cycloaddition of 1, 3-bis (trimethylsilyl) isobenzofuran (2) with arynes generated by LTMP-induced dehydrohalogenation of readily accessible haloaromatics. The cycloadducts undergo a novel acid-induced conversion to anthracenones. For several substrates this reaction is highly regioselective, allowing ...

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