Journal
JOURNAL OF HETEROCYCLIC CHEMISTRY
Volume 58, Issue 7, Pages 1531-1540Publisher
WILEY
DOI: 10.1002/jhet.4279
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N,N-diarylsubstituted 2-aminothiophenes are protonated at specific positions, while 5-formyl and 5-acetyl-substituted compounds are protonated at the corresponding carbonyl groups, facilitating the preparation of deuterated derivatives of amino thiophenes.
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.
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