The dilithium salt of tetraphenylbutadiene (1) reacts normally with phenyle
thynyltrichlorosilane to give 1-chloro-1-phenylethynyl-2,3,4,5-tetraphenyls
ilole (3), but with vinyltrichlorosilane the unexpected product is the sila
cycloheptadiene 2, and X-ray crystal structures were obtained for 2 and 3;
the seven-membered ring in 2 adopts a boat conformation, and a possible mec
hanism for the formation of 2 is suggested.