The chemistry and reactivity of aryl radicals - The C-C bond formation from o-bromobenzylphenylethers with tin hydride and azobisisobutyronitrile

Treatment of o-bromobenzylphenylethers and a two fold excess of n-tributyltin hydride (TBTH) with 0.5 to 0.6 mol equiv. of AIBN induces an inefficient C-aryl-C-aryl bond formation. The structures of the products resulting from a 1,5 and/or a 1,6 additions were found to be largely determined by the presence or absence of the substituent and its position in the phenyl ring. Copyright (C) 1996 Elsevier Science Ltd