Fluoronaphthalene building blocks via arynes: A solution to the problem of positional selectivity

E Masson, M Schlosser

Index: Masson, Eric; Schlosser, Manfred European Journal of Organic Chemistry, 2005 , # 20 p. 4401 - 4405

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Citation Number: 13

Abstract

Abstract When 3-fluoro-and 3-chloro-1, 2-didehydrobenzenes are generated in the presence of 2-(trimethylsilyl) furan, two regioisomeric cycloadducts are formed in a 1: 2 ratio. However, regioselectivity can be installed by fitting one bulky trimethylsilyl group into sterically critical positions of each of the two reaction components. Thus 3-fluoro-6- trimethylsilyl-1, 2-didehydrobenzene and 2-(trimethylsilyl) furan give one cycloadduct ...