Abstract Formation of both sila-functional and carbo-functional phenoxasilins from diphenyl ether and o, o′-dibromodiphenyl ether precursors is described. Tricyclic oxasilepins are formed from o, o′-dibromobenzylphenyl ether by metallation with n-BuLi followed by reaction with dichlorosilanes as well as by ring expansion of an appropriate phenoxasilin. Reactions at the silicon center and at the ring methylene carbon of the oxasilepins are ...