Reactions of lead tetra-acetate. Part XVIII. Oxidation of aldehyde hydrazones: a new method for the generation of nitrilimines
作者:W. A. F. Gladstone、J. B. Aylward、R. O. C. Norman
DOI:10.1039/j39690002587
日期:——
of the isomeric 4-carbonitrile. Analogous nitrilimines have been similarly trapped during the oxidation of the p-nitrophenylhydrazones of benzaldehyde, propionaldehyde, benzoin, and benzil. Oxidations with lead tetrabenzoate, and with lead tetra-acetate in methanol, have also been carried out; they lead to azo-dibenzoates and azo-dimethyl ethers, respectively, and benzaldehyde phenylhydrazone also forms
许多醛芳基hydr已被四乙酸铅氧化。在许多情况下,可以高收率分离出二酰基肼RCO·NH·NAcAr。如果采取了预防措施避免自氧化,则使用苯甲醛苯hydr,可以分离出产率高达27%的乙酸α-苯基偶氮苄基乙酸酯。已经获得的证据表明该化合物不是二酰基衍生物PhCO·NH·NAcPh或其他氧化产物的主要前体,而是通过腈亚胺PhC生成的。该1,3-偶极化合物已被丙烯腈截留,与少量异构体4-腈一起形成1,3-二苯基吡唑-5-腈。类似的腈亚胺在p的氧化过程中也被类似地捕获苯甲醛,丙醛,安息香和苯甲腈的-硝基苯基hydr。还已经进行了四苯甲酸铅和四乙酸铅在甲醇中的氧化。它们分别导致偶氮二苯甲酸酯和偶氮二甲醚,而苯甲醛苯hydr也形成了偶氮苯甲酸酯。