Journal of Organic Chemistry p. 129 - 135 (1988)
Update date:2022-07-30
Topics:
Kamitori, Yasuhiro
Hojo, Masaru
Masuda, Ryoichi
Fujitani, Toshihiko
Ohara, Seiji
Yokoyama, Tetsuya
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-acylated products.The trifluoroacetyl hydrazones can be cyclized thermally to imidazole and oxadiazine derivatives and can be converted into 1-trifluoromethyl 1,2-diketones by acid hydrolysis.
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