Reactivity of Bromodilithiosilane to Napthalene and Anthracene

Abstract

Bromodilithiosilane, 1, reacted with naphthalene at 110 degrees C to give the silacyclopropane derivative 2, which reacted with MeOH(D), Mel. and Me(3)SiCl to yield 3, 4, and 5 in 84%, 82%, and 85% yields, respectively, 1 also reacted with anthracene at -30 degrees C to give the lithio-silanorbornadiene derivatives, which were trapped by 1-PrOH to yield 6 and 7 as colorless crystals in 27% and 54%. These results show an important synthetic application of 1,1-dilithiosilane bearing a halogen atom, which differs from those of known 1,1-dilithiosilanes.