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

作　　者：Mohammad Ali Karimi Zarchi Saeed Barani 

机构地区：[1]Department of Chemistry,College of Sciences,Yazd University

出　　处：《Chinese Journal of Polymer Science》2013年第7期1002-1010,共9页高分子科学（英文版）

摘　　要：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.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. 

分 类 号：O631.3[理学—高分子化学]