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RAPID AND FACILE SYNTHESIS OF ACYL AZIDES FROM ACYL HALIDES USING A POLYMER-SUPPORTED AZIDE ION UNDER HETEROGENEOUS CONDITIONS

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Chinese Journal of Polymer Science 2013年第7期31卷 1002-1010页

作者： Mohammad Ali Karimi Zarchi saeed barani Department of Chemistry College of SciencesYazd University

In this article a rapid and facile method for synthesis of acyl azide is described. The cross-linked poly（N-methyl-4- vinylpyridinium） azide ion, [Pa-VP]N3 is prepared and used as an efficient polymeric reagent for synthesis of acyl azides from acyl halides at room temperature under heterogeneous conditions. Various benzoyl halides, with electron-withdrawing groups as well as electron-donating groups, were transformed into the corresponding benzoyl azides in high to excellent yields in short reaction times. The acyl azide products were characterized by FT-IR, and some of them were also characterized by IH- and/or 13C-NMR spectroscopy, and physical properties were compared to literature values of known compounds. The spent polymeric reagents can be regenerated and reused for several times without losing their activity. Relative to the reported methods, the present method has the advantages of operational simplicity, mild reaction conditions, fast reaction rates, simple reaction work-up and lower hazardous and potentially explosive nature. Also the present method is the first procedure for the synthesis of acyl azides from acyl halides by using a polymer-supported azide ion under heterogeneous conditions.

关键词： Acyl azide Acyl halide Polymeric reagent Heterogeneous condition.

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