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Temperature-controlled S vs N selective alkylation of 1-phenyl tetrazole-5-thione with α,β-unsaturated systems in solvent-free organic salt media.
- Source :
-
Journal of Sulfur Chemistry . Dec2023, Vol. 44 Issue 4, p479-493. 15p. - Publication Year :
- 2023
-
Abstract
- In this work, a novel series of N and S-alkylated derivatives of 1-phenyl tetrazole-5-thione were synthesized by Michael addition in organic salt media TBAB (Tetrabutylammonium bromide) using inorganic base K2CO3 under solvent-free conditions. The new and conveniently synthesized products showed unusual regioselectivity during the reaction. S-Michael adducts via reaction between 1-phenyl tetrazole-5-thione and acrylic esters as well as acrylonitrile were afforded at room temperature and N-Michael adducts obtained at 70°C. Both reactions occurred within 24 h. Surprisingly, using fumarate esters as Michael acceptor proceeded a SN2 reaction at 100°C due to steric effects. The structures of products all were confirmed by 1H and 13C NMR spectra and target compound yields were good to excellent. [ABSTRACT FROM AUTHOR]
- Subjects :
- *ALKYLATION
*SALT
*REGIOSELECTIVITY (Chemistry)
*BROMIDES
*ESTERS
Subjects
Details
- Language :
- English
- ISSN :
- 17415993
- Volume :
- 44
- Issue :
- 4
- Database :
- Academic Search Index
- Journal :
- Journal of Sulfur Chemistry
- Publication Type :
- Academic Journal
- Accession number :
- 164492163
- Full Text :
- https://doi.org/10.1080/17415993.2023.2173010