1,4-bis[2,2-bis(trimethylsilyl)ethenyl]benzene: Regioselective ring opening of its α,β-epoxybis(silane) with some nucleophiles

The Peterson olefination reaction of terephthalaldehyde with tris(trimethylsilyl)methyllithium, (Me3Si)3CLi, in Et2O gives disubstituted vinylbis(silane) 1 which reacts with MCPBA in CH2Cl2 at r.t. to afford mixture of mono and disubstituted epoxybis(silanes) 3 and 2. Vinylbis(silane) 1 can be completely converted into epoxybis(silane) 2 with an excess amount of MCPBA. The compound 2 was reacted with various reagents such as HX (X = Cl, Br), H2SO4, LiAlH4 and MeLi/CuI and give the related products.

Graphical abstractVinylbis(silane) 1 which reacts with MCPBA in CH2Cl2 at r.t. to afford mixture of mono and disubstituted epoxybis(silanes) 3 and 2. The compound 2 was reacted with various reagents such as HX (X=Cl, Br), H2SO4, LiAlH4 and MeLi/CuI and give the related products.Figure optionsDownload full-size imageDownload as PowerPoint slide