Electrochemical synthesis of symmetrical difunctional disilanes as precursors for organofunctional silanes

Difunctional disilanes of the general type XR2SiSiR2X (1–5) (X = OMe, H; R = Me, Ph, H) have been synthesized by electrolysis of the appropriate chlorosilanes XR2SiCl in an undivided cell with a constant current supply and in the absence of any complexing agent. Reduction potentials of the chlorosilane starting materials derived from cyclic voltammetry measurements were used to rationalize the results of preparative electrolyses. Organofunctional silanes of the general formula MeO(Me2)SiC6H4Y (6a–c, 7) were subsequently obtained by the reaction of sym-dimethoxytetramethyldisilane (1) with NaOMe in the presence of p-functional aryl bromides BrC6H4Y (Y = OMe, NEt2, NH2).

Graphical abstractDifunctional disilanes XR2SiSiR2X (X = OMe, H; R = Me, Ph, H) have been synthesized by electrolysis of the appropriate chlorosilanes HR2SiCl. The results of preparative electrolyses were rationalized by cyclic voltammetry measurements. The reaction of MeOMe2SiSiMe2OMe with NaOMe in the presence of functional aryl bromides BrC6H6Y (Y = OMe, NEt2, NH2) affords organofunctional silanes MeO(Me2)SiC6H6Y.Figure optionsDownload full-size imageDownload as PowerPoint slide