Reaction of aryl Grignard reagents with hexahalobenzenes: Novel arenes via multiple aryne sequence

K Harada, H Hart, CJ Frank Du

Index: Harada, Katsumasa; Hart, Harold; Du, Chi-Jen Frank Journal of Organic Chemistry, 1985 , vol. 50, # 26 p. 5524 - 5528

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Citation Number: 37

Abstract

We recently described2 a new p-terphenyl synthesis that proceeds according to the sequence in Scheme I. The reaction exhibits several interesting features pertinent to the present work:(a) 4 equiv of aryl Grignard are required per mole of 1-2 are used in exchange reactions to form monoGrignard 2 and diGrignard 3, and 2 furnish the “outside” aryl rings of the product 6;(b) novel organometallic arynes such as 4 are intermediates;(c) nucleophilic ...