Functional group transformations of 7-silabenzonorbornadiene derivatives have been investigated. The 7-mesityl-7-silanorbornadiene 1 was prepared and converted into the 7-chloro derivative 5. Reductive lithiation of 5 with lithium naphthalenide afforded the silyllithium 6, which reacted with Me3SiCl and MeI. The reactions of 5 with n-BuLi and PhNHLi gave the 7-butyl derivative 9 and the 7-amino derivative 10, respectively. Each stereochemistry during these transformations was determined by X-ray crystallographic analysis.