Electrophilic substitution at azomethine carbon atoms. Reaction of aromatic aldehyde hydrazones with trifluoroacetic anhydride

Y Kamitori, M Hojo, R Masuda, T Fujitani…

文献索引：Kamitori, Yasuhiro; Hojo, Masaru; Masuda, Ryoichi; Fujitani, Toshihiko; Ohara, Seiji; Yokoyama, Tetsuya Journal of Organic Chemistry, 1988 , vol. 53, # 1 p. 129 - 135

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被引用次数: 65

摘要

Reaction of dimethylhydrazones of aromatic aldehydes with trifluoroacetic anhydride at room temperature affords high yields of products bearing trifluoroacetyl groups. These electrophilic substitution reactions generally occur on the azomethine carbon, although competitive N-acylation is observed in highly electron-rich systems. Use of diisopropylhydrazones suppressed this N-acylation completely, leading to high yields of C ...