Stable Silapyramidanes

Abstract

Starting from tetrakis(trimethylsilyl)cyclobutadiene and an amidinate-supported silylene of the Roesky-type, a sequence of addition and reduction cleanly gives the elusive silapyramidane via an isolable cyclobutene intermediate with an exocyclic Si═C bond. The silapyramidane features an unusually shielded ²⁹Si NMR resonance at -448.3 ppm for the apex silicon atom. Treatment with Fe₂(CO)₉ results in the formation of the corresponding silapyramidane-iron complex. Silapyramidane also reacts with the cyclobutadiene starting material to cleanly afford a fluorescent spirobis(silole).