Photolysis of ((3-Trimethylsilyl)propoxy)phenyl) phenyliodonium salts in the presence of 1-naphthol and 1-methoxynaphthalene

Direct photolysis of ((3-trimethylsilylpropoxy)phenyl)phenyliodonium salts with different counteranions (Cl-, SbF6-, and B(C6F5)(4)(-)) in methanol le ads to products by both heterolytic and homolytic processes. In the presenc e of 1-naphthol and 1-methoxynaphthalene, products formed by a heterolytic reaction disappear, suggesting an electron-transfer process occurs between excited 1-naphthol/1-methoxynaphthalene and the iodonium salts. In the case of 1-methoxynaphthalene, three phenylated methoxynaphthalene isomers are p roduced. These are produced as radical coupling products from the phenyl ra dical and 1-methoxynaphthalene radical cation.