Reactivity of Bromodilithiosilane to Naphthalene and Anthracene

Bromodilithiosilane, 1, reacted with naphthalene at 110 °C to give the silacyclopropane derivative 2, which reacted with MeOH(D), MeI, and Me3SiCl to yield 3, 4, and 5 in 84%, 82%, and 85% yields, respectively. 1 also reacted with anthracene at −30 °C to give the lithio-silanorbornadiene derivatives, which were trapped by i-PrOH to yield 6 and 7 as colorless crystals in 27% and 54%. These results show an important synthetic application of a 1,1-dilithiosilane bearing a halogen atom, which differs from those of known 1,1-dilithiosilanes.