Silicon–Carbon Unsaturated Compounds. XVI. Photorearrangement of an Adduct Derived from Reaction of a Silicon–Carbon Unsaturated Compound with <i>t</i>-Butyl Alcohol

Abstract

Abstract Photolysis of pentamethylphenyldisilane in the presence of t-butyl alcohol gave a mixture of adducts which were readily oxidized to 1-(t-butoxydimethylsilyl)-2-(trimethylsilyl)benzene by oxygen. Photolysis of p-tolylpentamethyldisilane in the presence of t-butyl alcohol afforded 4-(t-butoxydimethylsilyl)-1-methyl-5-trimethylsilyl-1,3-cyclohexadiene (4) as a primary photoproduct. The UV-irradiation of 4 gave ring opened products, 2-(t-butoxydimethylsilyl)-5-methyl-1-trimethylsilyl-1,3,5-hexatriene and 2-(t-butoxydimethylsilyl)-5-methyl-3-trimethylsilyl-1,3,5-hexatriene in a ratio of 1.8/1.