Using a polymer-supported azide ion in [2+3] cycloaddition reaction of azide ion with nitriles

The [2+3] cycloaddition between various nitriles and crosslinked poly(4‐vinylpyridine) supported azide ion proceeds smoothly in the presence of ammonium bromide or ammonium chloride in N,N‐dimethyl formamide, to give the corresponding 5‐substituted‐1H‐tetrazoles in good to high yields. Conventional...

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Bibliographic Details
Published in:Journal of applied polymer science 2012-02, Vol.123 (4), p.1977-1982
Main Authors: Karimi Zarchi, Mohammad Ali, Nazem, Fatemeh
Format: Article
Language:English
Subjects:
5-substituted 1-H tetrazole
[2+3] cycloaddition
alkyl azide
Ammonium bromides
Ammonium chlorides
Applied sciences
Crosslinking
Cycloaddition
Exact sciences and technology
Heating
Materials science
nitrile
Nitriles
Organic polymers
Physicochemistry of polymers
polymer-supported reagent
polymeric reagent
Polymers
Properties and characterization
Reaction time
Special properties (catalyst, reagent or carrier)
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Summary:The [2+3] cycloaddition between various nitriles and crosslinked poly(4‐vinylpyridine) supported azide ion proceeds smoothly in the presence of ammonium bromide or ammonium chloride in N,N‐dimethyl formamide, to give the corresponding 5‐substituted‐1H‐tetrazoles in good to high yields. Conventional heating was used to promote reaction. It was found that using nitriles with electron‐withdrawing groups result in bout higher yields and lower reaction times. The present procedure offers advantages, such as shorter reaction time, and simple workup. © 2011 Wiley Periodicals, Inc. J Appl Polym Sci, 2012
ISSN:0021-8995
1097-4628
1097-4628
DOI:10.1002/app.34701