Synthesis of new imines and amines containing organosilicon groups

The Peterson olefination reaction of terephthalaldehyde with tris(trimethylsilyl) methyl lithium, (Me3Si)(3)CLi, in THF at 0 degrees C gives 4-[2,2-bis(trimethylsilyl)ethenyl]benzaldehyde (1) and 4,4-bis[2,2-bis(trimethylsilyl)ethenyl]benzene (2). The new aldehyde (1) reacts with variety of amines in ethanol to afford the corresponding imines (3) containing vinylbis(trimethylsilyl) group. The newly synthesized imines (3) can be completely converted into amines containing vinylbis(trimethylsilyl) group with an excess amount of NaBH4. In the case of N-[4-(2,2-bis(trimethylsilyl)ethenyl)benzyl]-2,6-dimethylaniline LiAlH4 was used as a reducing agent in THF. (C) 2010 Elsevier B.V. All rights reserved.