Preparation of aryl cyanides from haloaromatics

SECTION 7.3 SUBSTITUTIONS INVOLVING ARYL FREE RADICALS 

Williams, Homolytic Aromatic Substitution, Pergamon Press, London, 1960 D. H. Hey, Adv. Free-Radical Chem. 2, 47 (1966). 

Sdieme 7.10. Aromatic Substitiitioii Involving Radical Intermediates 

Aryl radicals can also be used to introduce alkyl substituents onto aromatic rings. The aryl radical is generated by copper-catalyzed decomposition of an aryl diazonium ion and attacks an alkene. The radical that results is oxidized by Cu(II), 

Homolytic aromatic substitution can also occur via electron-transfer reactions, even in the absence of transition-metal catalysts. For example, irradiation of a liquid ammonia solution of acetone enolate with any of the halobenzenes results in the 

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Scheme 7.9. Preparation of Aryl Cyanides from Haloaromatics... 

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