Ag. Brook et al., 1,2-BIS(TRIMETHYLSILYL)-1,2-DIMESITYLETHENE - FORMATION FROM 1,1-DIMESITYL-2-BROMOETHENE, Organometallics, 16(19), 1997, pp. 4226-4228
Treatment of 1,1-dimesityl-2-bromoethene in ether at room temperature
with n-butyllithium gave rise to 1,2-dimesitylacetylene, which when tr
eated with lithium and trimethylchlorosilane formed (E)-1,2-bis(trimet
hylsilyl)-1,2-dimesitylethene in quantitative yield. In contrast, trea
tment of the bromoethene at -78 degrees C with n-butyllithium in THF (
but not either) results in halogen-metal exchange: the resulting organ
olithium reagent was trapped with trimethylchlorosilane.