STUDY OF THE MECHANISM OF THE OXIDATIVE CYCLIZATION OF BENZALDEHYDE SEMICARBAZONES INDUCED BY CUPRIC PERCHLORATE IN ACETONITRILE

被引:18
作者
NOTO, R
GRUTTADAURIA, M
LOMEO, P
FRENNA, V
WERBER, G
机构
[1] Dipartimento di Chimica Organica, Università di Palermo, Palermo, 90123
关键词
D O I
10.1002/jhet.5570320430
中图分类号
O62 [有机化学];
学科分类号
070303 ; 081704 ;
摘要
Treatment of benzaldebyde semicarbazones 1a-i with cupric perchlorate in acetonitrile at 40 degrees provided selectively the corresponding 1,2,4-triazolin-5-ones 2a-i. The relative rate constants for 2a-i formation were determined by the competitive method. The results obtained showed that electron-donating substituents (methyl and methoxy) increase the reaction rate, while the reverse was found for electron-withdrawing substituents (chloro and nitro group). The reactivity data are discussed on the grounds of two possible mechanisms.
引用
收藏
页码:1277 / 1282
页数:6
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