A Stable Bicyclic Compound with Two Si=Si Double Bonds

Abstract

In contrast to carbon, silicon does not readily form double bonds, and compounds containing silicon-silicon double bonds can usually be stabilized only by protection with bulky substituents. We have isolated a silicon analog of spiropentadiene 1 , a carbon double-ring compound that has not been isolated to date. In the crystal structure of tetrakis[tri( t -butyldimethylsilyl)silyl]spiropentasiladiene 2 , a substantial deviation from the perpendicular arrangement of the two rings is observed, and the silicon-silicon double bonds are shown to be distorted. Spectroscopic data indicate pronounced interaction between two remote silicon-silicon double bonds in the molecule. Silicon-silicon bonds may be more accessible to synthesis than previously assumed.