Azo coupling of 4-nitrophenyldiazonium chloride with aliphatic nucleophiles: an integrated organic synthesis and X-ray crystallography experiment

Química Nova

Universidade Federal de Goiás, Goiânia, Brasil¹  Rocha, Valéria¹  Universidade Federal da Bahia, Salvador, Brasil¹  Cunha, Silvio¹  Lariucci, Carlito¹  Marques, Monique F.¹  Vencato, Ivo¹ 

关键词: enaminone;    azo dye;    solid state structure.;   

DOI  :  10.1590/S0100-40422013000900029

学科分类：化学（综合）

来源: Sociedade Brasileira de Quimica

【 摘 要 】

This article describes an undergraduate experiment for the synthesis of p-nitrophenyldiazonium chloride and its coupling with acetylacetone and two enaminones, 4-phenylamino-pent-3-en-2-one and 4-amino-pent-3-en-2-one, in an adaptation of a previously reported synthetic protocol. The azo dyes 4-(E)-phenylamino-3-[(E)-2-(4-nitrophenylazo)]-3-penten-2-one and 4-(E)-amino-3-[(E)-2-(4-nitrophenylazo)]-3-penten-2-one were obtained, and the solid state structure of this latter azo compound was characterized by single crystal X-ray diffraction studies. This two-week integrated laboratory approach involves simple synthetic experiments and microwave chemistry in the organic laboratory plus crystallography analysis, suitable for novice students on undergraduate  experimental chemistry courses.

【 授权许可】

Unknown