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Synthesis of 2-(Benzylthio)-4-(trifluoromethyl)thiazole-5-carboxylates using S -benzylisothiouronium halides as thiol equivalents

Hickey, Shane M., White, Jonathan M., Pfeffer, Frederick M. and Ashton, Trent D. 2015, Synthesis of 2-(Benzylthio)-4-(trifluoromethyl)thiazole-5-carboxylates using S -benzylisothiouronium halides as thiol equivalents, Synlett: accounts and rapid communications in synthetic organic chemistry, vol. 26, no. 12, pp. 1759-1763, doi: 10.1055/s-0034-1380748.

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Title Synthesis of 2-(Benzylthio)-4-(trifluoromethyl)thiazole-5-carboxylates using S -benzylisothiouronium halides as thiol equivalents
Author(s) Hickey, Shane M.
White, Jonathan M.
Pfeffer, Frederick M.ORCID iD for Pfeffer, Frederick M. orcid.org/0000-0002-5441-6437
Ashton, Trent D.ORCID iD for Ashton, Trent D. orcid.org/0000-0002-6707-6064
Journal name Synlett: accounts and rapid communications in synthetic organic chemistry
Volume number 26
Issue number 12
Start page 1759
End page 1763
Total pages 5
Publisher Georg Thieme
Place of publication Stuttgart, Germany
Publication date 2015-07-01
ISSN 0936-5214
1437-2096
Keyword(s) 19F NMR spectroscopy
isothiouronium halide
nucleophilic aromatic substitution
thiazole
thioether
Science & Technology
Physical Sciences
Chemistry, Organic
Chemistry
F-19 NMR spectroscopy
ONE-POT SYNTHESIS
FUNCTIONALIZED MESOPOROUS SBA-15
IN-SITU GENERATION
ALKYLISOTHIOURONIUM SALTS
BIOLOGICAL-ACTIVITY
MICHAEL ADDITION
ORGANIC HALIDES
ARYL HALIDES
ODORLESS
THIOETHERS
Summary S-Benzylisothiouronium halides are used as shelf-stable, odorless thiol equivalents. The method developed is used to access 2-(benzylthio)-4-(trifluoromethyl)thiazole carboxyl building blocks. Using the latent trifluoromethyl substituent the reactions could be monitored using 19F NMR spectroscopy.
Language eng
DOI 10.1055/s-0034-1380748
Field of Research 0305 Organic Chemistry
030503 Organic Chemical Synthesis
Socio Economic Objective 970103 Expanding Knowledge in the Chemical Sciences
HERDC Research category C1 Refereed article in a scholarly journal
Copyright notice ©2015, Georg Thieme
Persistent URL http://hdl.handle.net/10536/DRO/DU:30075595

Document type: Journal Article
Collection: School of Life and Environmental Sciences
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Created: Fri, 27 Nov 2015, 10:43:02 EST

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