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8498641 
Journal Article 
Nitrations of N-Trifluoroacetyl Aromatic Amines 
Fukunaga, K; Yoshida, T; Kimura, M 
1976 
1 
Nippon Kagaku Kaishi
ISSN: 0369-4577
EISSN: 2185-0925 
CHEMICAL SOC JAPAN 
TOKYO 
1976 
1 
133-137 
English 
WOS:A1976BC82600025 
Nitrations of N-trifluoroacetyl aromatic amines (Ar-NHCOCF3) were studied in comparison with those of N-aeetyl aromatic amines (Ar-NHCOCH3). The substituent -NHCOCF3 was an o, p-orienting group in analogy with the substituent -NHCOCH3 in nitrations of Ar-NHCOCF3 (Ar = phenyl or naphthyl groups) (Table 2). However, these substituents showed the reverse orienting influences in nitrations of p-RCONH-biphenyl ([9]; R=CF3, [9']; R = CH3), 2-RCONH-fluorene ([12]; R = CF3, [12']; R = CH3), and 3-RCONH-dibenzofuran ([13]; R = CF3, [13']; R = CH3) (Table 3). These curious effects of the substituent -NHCOCF3 are considered to be due to the interaction between inductive effects, resonance effects, and the electrostatic repulsion induced in the course of the ortho attack. © 1976, The Chemical Society of Japan. All rights reserved.