574751-77-2Relevant academic research and scientific papers
An unusual behaviour of N-(tert-butoxycarbonyl)- and N-pivaloyl-(methylthio)anilines in metallation reactions
Cabiddu, Maria Grazia,Cabiddu, Salvatore,Cadoni, Enzo,De Montis, Stefania,Fattuoni, Claudia,Melis, Stefana
, p. 2893 - 2897 (2007/10/03)
The metallation reaction of N-Boc-and N-Piv-(methylthio)anilines are here described. The results show that N-Boc derivatives are metallated only by superbases to give products substituted at the thiomethylic group. N-Piv derivatives show a different behaviour: ortho-derivative is metallated by both butyllithium and superbase at the thiomethylic carbon atom, while para-derivative is metallated in ortho to the N-Piv group by butyllithium and at the thiomethylic carbon atom by superbase. The meta-derivative is metallated only by superbase at the thiomethylic carbon atom.
