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Several functional dibenzosilole compounds, i.e., compounds having a silicon-chlorine bond, as well as some non-functional dibenzosilole types, have been prepared by a cyclization reaction from 2,2'-biphenylenedilithium and appropriately substituted R2SiCl2 or RS1CI3 compounds. Also, 5,5'-spirobi[dibenzosilole] and 5,5'-spirobi[dibenzogermole] have been synthesized in a similar fashion from silicon tetrachloride and germanium tetrachloride, respectively. The functional dibenzosilole derivatives have been treated with a variety of organolithium reagents to yield non-functional dibenzosilole compounds, some of which appear to possess favorable thermal stability characteristics.

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