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

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

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

Full Text: HTML

Citation Number: 65

Abstract

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 ...

Related Articles:

Palladium??Catalyzed Reductive Carbonylation of Aryl Bromides with Phosphinite Ligands

[Neumann, Helfried; Kadyrov, Renat; Wu, Xiao-Feng; Beller, Matthias Chemistry - An Asian Journal, 2012 , vol. 7, # 10 p. 2213 - 2216]

Secondary amine catalyzed retro-aldol reactions of enals and enones: one-pot conversion of enals to α-substituted derivatives

[Enders, Dieter; Nguyen, Thanh V. Tetrahedron Letters, 2012 , vol. 53, # 16 p. 2091 - 2095]

Novel synthesis of 3, 6-disubstituted-1, 2, 4, 5-tetrazine derivatives from hydrazones by using [hydroxyl (tosyloxy) iodo] benzene

[Liu, Haixuan; Wei, Yunyang Tetrahedron Letters, 2013 , vol. 54, # 35 p. 4645 - 4648]

Cooperative catalysis of palladium nanoparticles and cobalt oxide support for formylation of aryl iodides under syngas atmosphere

[Hamasaki, Akiyuki; Yasutake, Yutaro; Norio, Takafumi; Ishida, Tamao; Akita, Tomoki; Ohashi, Hironori; Yokoyama, Takushi; Honma, Tetsuo; Tokunaga, Makoto Applied Catalysis A: General, 2014 , vol. 469, p. 146 - 152]

Clean and selective oxidation of aromatic alcohols using silica-supported Jones' reagent in a pressure-driven flow reactor

[Wiles, Charlotte; Watts, Paul; Haswell, Stephen J. Tetrahedron Letters, 2006 , vol. 47, # 30 p. 5261 - 5264]

More Articles...