STUDIES ON THE THERMAL-ISOMERIZATION OF N-ARYLMETHYLBENZOTRIAZOLES

被引:29
作者
KATRITZKY, AR
PERUMAL, S
FAN, WQ
机构
[1] Department of Chemistry, University of Florida, Gainesville
来源
JOURNAL OF THE CHEMICAL SOCIETY-PERKIN TRANSACTIONS 2 | 1990年 / 12期
关键词
D O I
10.1039/p29900002059
中图分类号
O62 [有机化学];
学科分类号
070303 ; 081704 ;
摘要
The thermal isomerizations of N-benzyl-, N-diarylmethyl- and N-trityl-benzotriazole, and of N-[bis-4-methoxyphenyl)methyl]- and N-trityl-5,6-dimethylbenzotriazole under nitrogen have been investigated. In all these cases, the N-1 isomer predominates over the N-2 isomer at thermodynamic equilibrium, to an extent which depends on the steric bulk of the N-substituent. The rate of attainment of equilibrium depends on the electronic effects of the substituents, both in the benzotriazole ring and in the migrating group. These results, in conjunction with a cross-over experiment, support a mechanism involving a heterolytic N-C bond cleavage followed by an intermolecular rearrangement.
引用
收藏
页码:2059 / 2062
页数:4
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