Study on the Silylation of Aromatic Hydrocarbons. The Trimethylsilylation of Naphthalene

Direct trimethylsilylation of naphthalene under certain condition has been found to afford substitution as well as addition products: 1-and 2-trimethylsilylnaphtalene (I, II), 1-trimethylsilyl-1,4-dihydronaphthalene (III), trans-1,2-bis(trimethylsilyl)-1,2-dihydronaphthalene (IV-a) and its isomer (IV-b), and 1,2,4-tris(trimethylsilyl)-1,2-dihydronaphthalene (V). The configuration has been determined by nmr spectroscopy, and the possible reaction path was proposed.