Lithium carbenoids induced ring enlargement of silacyclobutane into 2-halo-1-silacyclopentane and its use in organic synthesis
摘要:
An addition of lithium diisopropylamide to a solution of 1,1-dimethyl-1-silacyclobutane and dihalomethane such as CH2I2, CH2Br2, or CH2Cl2 Provided the corresponding 1,1-dimethyl-2-halo-1-silacyclopentane in good yield. The reactions of 1,1,2-trimethyl-1-silacyclobutane or 1,1,3-trimethyl-1-silacyclobutane with lithium carbenoids are also described. Treatment of 2-iodo-1-silacyclopentane with tert-butyllithium gave 2-lithio-1-silacyclopentane which reacted with electrophiles to afford the corresponding adducts.
Stereoselective formation of silacyclopentanes by the reaction of silacyclobutane with lithium carbenoids
作者:Kozo Matsumoto、Koichiro Oshima、Kiitiro Utimoto
DOI:10.1016/s0040-4039(00)98027-4
日期:——
An addition of lithium diisopropylamide to a solution of 1,1-dimethyl-1-silacyclobutane and diiodomethane provided 1,1-dimethyl-2-iodo-1-silacyclopentane in good yield.
Whereas the reaction of 1,1-dimethyl-1-silacyclobutane (1a) with dimethyl acetylenedicarboxylate in the presence of Pd catalyst provides dimethyl 1,1-dimethyl-1-sila-2-cyclohexene-2,3-dicarboxylate...