Trimethylsilyl Compounds as General Synthesis Reagents

Various nitrogen compounds can be obtained from aminotrimethylsilanes if the N—Si bond is easily converted to an N—C, N—S, N—B or other N—El bonds. An example of this method of formation of an N—C bond is the preparation of /-dimethylaminocyclohexene [592] (Eq. 4.50). 

Ethers also react with iodotrimethylsilane, and form iodomethyl ether [599] e.g. Eq. 4.54  

Some organic compounds can be converted with hexamethyldisilane and iodine (2-3 h at 60°C in chloroform formation of iodotrimethylsilane in situ) into their a-iodo derivatives [600], e.g. 

With potassium hydride the configuration is retained with boron trifluoride or sulphuric acid, it is inverted. 

1-Alkenes can be converted into 1-haloalkanes. The olefins first react with trichlorosilane, and then with potassium fluoride. The halogenation of alkylpen-tafluorosilicates yields 1-haloalkanes [602] (Eq. 4.55)  

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