Gas chromatography coupled with tandem mass spectrometry analysis constitutes a powerful tool to characterize a series of (poly)trimethylsilyl derivatives of naphthalene, formed by electrochemical reduction of 1-bromonaphthalene in the presence of trimethylchlorosilane in large excess. From the relationship preliminarily established between structures of products resulting from the silylation of benzene and naphthalene derivatives, and their fragmentations in mass spectrometry, the formation of quite unexpected naphthalenes bearing two trimethylsilyl groups at the peri position has been established. Moreover, heptakis and octakis(trimethylsilylated) species, in which all the trimethylsilyl groups are directly bonded to the bicyclic skeleton, have been detected for the first time. #

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