Halogen-silyl-austausch am amid-stickstoff

The Use of Bis(trimethylsilyl)acetamide and Bis (trimethylsilyl)urea for Protection and as Control Reagents in Synthesis

“…BSA has been formulated as the N,N-bis(trimethylsilyl)acetamide as well as in the imidate form. However, nuclear magnetic resonance spectra ( 13 C, 29 Si, 14 N, 15 N, and 17 O) of a number of silylamide derivatives have been investigated and the results allow an unambiguous assignment of their structures. 8 Whereas BSA is seen to exist in the imidate form, some others, for example bis(trimethylsilyl)formamide and BSU, exist in the N,N-bis(trimethylsilyl) form and the product obtained by the interaction of bis-1,2-(chlorodimethylsilyl)ethane with BSA is also clearly in the alternative form.…”

“…One of the early reported uses of BSA involved the conversion of N-haloamides into the Nhaloimidic trimethylsilyl esters, for example N-chloroacetamide into N-chloroacetimidic trimethylsilyl ester. 15 Part per billion traces of environmentally important phenols and carboxylic acids in water have been determined by concentration using macroreticular resins and subsequent derivatisation using BSA before gas chromatography. 16 The protection of phenols were among the first examples of the use of BSA, including the trimethylsilylation of 2,6di-t-butylphenol.…”