Synthesis and Transformations of 2,4,4,7-Tetramethyl-4-silanaphtho[3,2-b]thiophen-9-one

The catalytic dehydrocyclization of dimethyl(5-methyl-2-thienyl)(2,4-dimethylphenyl)silane accompanied by a skeletal rearrangement gives 2,4,4,7-tetramethyl-4,9-dihydro-4-silanaphtho3,2-b]thiophene, which was oxidized to 2,4,4,7-tetramethyl-4-silanaphtho3,2-b]thiophen-9-one, whose structure was solved by X-ray diffraction structural analysis. Various chemical transformations of the ketone synthesized were performed including radical bromination by bromosuccinimide, condensation with furfural in the presence of KOH, reduction by LiAlH₄, and nitration by acetyl nitrate.