Preparation of 5-alkylthio and 5-arylthiotetrazoles from thiocyanates using phase transfer catalysis

Article abstract of DOI:10.1080/00397919808004905

A very efficient method of preparation for 5-alkyl and 5- arylthiotetrazoles from the corresponding alkyl or aryl halides is described. The halides are first transformed into thiocyanates which further react with azide, yielding the corresponding tetrazoles with [2+3] polar cycloaddition. All synthetic transformations are performed under phase transfer catalytic conditions. The yields vary from good to excellent except for the preparation of 5-benzylthiotetrazole, where the reaction between benzyl thiocyanate and azide [2+3] cycloaddition is in competition with nucleophilic substitution, with benzyl azide as product.

Full text of DOI:10.1080/00397919808004905

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Synthetic Communications:
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Preparation of 5-Alkylthio
and 5-Arylthiotetrazoles
from Thiocyanates Using
Phase Transfer Catalysis
Blaise W. LeBlanc a & Branko S. Jursic a
a Department of Chemistry, University of New
Orleans, New Orleans, Louisiana, 70148
Version of record first published: 22 Aug 2006.
To cite this article: Blaise W. LeBlanc & Branko S. Jursic (1998): Preparation
of 5-Alkylthio and 5-Arylthiotetrazoles from Thiocyanates Using Phase Transfer
Catalysis, Synthetic Communications: An International Journal for Rapid
Communication of Synthetic Organic Chemistry, 28:19, 3591-3599
To link to this article: http://dx.doi.org/10.1080/00397919808004905
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