Abstract
Trimethylsilylation of secondary amines by the common reagent N,O-bis(trimethylsilyl)trifluoroacetamide (BSTFA) in the presence of dimethylformamide (DMF) produces the previously unknown N-(aminomethylene)-2,2,2-triftuoroacetamide (AMT) derivative, in addition to the trimethylsilyl derivative. This derivative is formed in varying yield by incorporation of CH atoms from DMF, and a CF 3CO group from BSTFA. The structure of the AMT moiety was characterized in the nucleic acid base queuine using stable isotopic labeling, high-resolution mass spectrometry, and 13C and 19F nuclear magnetic resonance spectroscopy. The AMT derivative has unexplored potential for use in gas chromatography and mass spectrometry but its formation may otherwise be undesirable, suggesting that the combined use of BSTFA and DMF be used with caution for silylation of compounds containing secondary amino groups.
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