On the protonation and deuteration of N,N-disubstituted 2-aminothiophenes, 2-aminothiazoles,and some 3-amino substituted analogues |
| |
Authors: | Christoph Heichert Horst Hartmann |
| |
Affiliation: | Fakultät Chemie und Lebensmittelchemie, Technische Universität Dresden, Dresden, Germany |
| |
Abstract: | In contrast to their carbocyclic aniline analogues, N,N-diarylsubtituted 2-aminothiophenes are not protonated at their N-atoms but at the 5-position or, to a smaller extent, at the 3-position of the thiophene nucleus giving rise to cationic species of the Wheland type. However, 5-formyl and 5-acetyl-substituted 2-(N,N-diarylamino)thiophenes are protonated at the corresponding carbonyl moieties. This finding not only enables insight into the mechanism of electrophilic substitution of N,N-disubstituted 2-aminothiophenes but also allows to prepare deurated 2-aminothiophenes by treatment their non-deuterated parent compounds with CF3COOD. |
| |
Keywords: | |
|
|