The effect of the γ-OMe group on the reactivity of the germanium chloride (Me3Si)2C(SiMe2OMe)(GeMe2Cl)

Abstract

The germanium chloride (Me₃Si)₂C(SiMe₂OMe)(GeMe₂Cl)(2a) has been found to be much more reactive than the related chloride (Me₃Si)₃C(GeMe₂Cl)(1) towards silver salts. The compound (Me₃Si)₂C(SiMe₂OMe)(GeMe₃) is correspondingly much more reactive than (Me₃Si)₃C(GeMe₃) towards CF₃CO₂H. These findings are consistent with anchimeric assistance by the γ-OMe group to leaving of Cl^– or Me^–, but a firm conclusion that such an effect operates was prevented by the finding that (2a) is also much more reactive than (1) towards NaOMe–MeOH. The methanolysis of (2a) in NaOMe–MeOH differs mechanistically from that of the analogous silicon chloride (Me₃Si)₂C-(SiMe₂OMe)(SiMe₂Cl).