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Transalkylation and Migration of N-Substituent upon Alkylation of 1,2,3-Triazoles Containing Good Leaving N-Substituents.
- Source :
-
European Journal of Organic Chemistry . Dec2016, Vol. 2016 Issue 35, p5897-5906. 10p. - Publication Year :
- 2016
-
Abstract
- The synthesis of four new 1,2,3-triazole derivatives and seven 1,2,3-triazolium salts that contain an organometallic group (i.e., cymantrenyl and ferrocenyl) at either the N-1, N-2, or N-3 position was realized. The alkylation of organometallic and organic triazole derivatives was investigated, and as a result of these studies, it was found that the presence of a good leaving group at the heterocyclic nitrogen atom led to transalkylation and subsequent migration of the N-1 substituent to the N-2 position of the triazole moiety. The nucleophilicity of the counterion of the triazolium salt influenced the transalkylation and isomerization processes, which suggests that the elimination of the N-substituent most likely occurs though a concerted mechanism with nucleophilic assistance from the counterion. Thus, a new approach to the synthesis of 2,4-disubstituted 1,2,3-triazoles has been developed. [ABSTRACT FROM AUTHOR]
Details
- Language :
- English
- ISSN :
- 1434193X
- Volume :
- 2016
- Issue :
- 35
- Database :
- Academic Search Index
- Journal :
- European Journal of Organic Chemistry
- Publication Type :
- Academic Journal
- Accession number :
- 120214242
- Full Text :
- https://doi.org/10.1002/ejoc.201601146