Reinvestigation of the Lewis acid catalyzed rearrangement of someopen-chain permethyloligosilanes with the Al(Fe)Cl(3) catalyst system exhibited several cases of additional reactivity: namely, a fragmentation/cyclization reaction. Introduction of (trimethylsilyl)methyl substituents into the oligosilane substrates strongly facilitated this reaction, yielding cyclic or bicyclic carbacyclosilanes. Investigations concerning