PHOTOLYSIS OF 2-METHYL-5-PHENYLTETRAZOLE

被引:18
作者
FRASER, RR
GURUDATA
HAQUE, KE
机构
[1] Department of Chemistry, University of Ottawa, Ottawa
关键词
D O I
10.1021/jo01264a077
中图分类号
O62 [有机化学];
学科分类号
070303 ; 081704 ;
摘要
The photolysis of 2-methyl-5-phenyltetrazole has been found to produce 2-methyl-4,5-diphenyl-1,2,3-triazole (2) in 22-27% yield and 1,2-di(methylazo)-1,2-diphenylethylene (3) in 6-10% yield. In contrast to previous studies on the photolytic behavior of tetrazoles, no evidence of production of a nitrilimine was found. The product formation is rationalized via an intermediate photodimer. The structure of the triazole was confirmed by an independent synthesis, while the structural assignment for the bisazoethylene rests on spectral evidence. © 1969, American Chemical Society. All rights reserved.
引用
收藏
页码:4118 / &
相关论文
共 27 条
[11]  
HAQUE KE, 1966, THESIS U OTTAWA
[12]   RINGOFFNUNGEN DER AZOLE .6. DIE THERMOLYSE 2.5-DISUBSTITUIERTER TETRAZOLE ZU NITRILIMINEN [J].
HUISGEN, R ;
SAUER, J ;
SEIDEL, M .
CHEMISCHE BERICHTE-RECUEIL, 1961, 94 (09) :2503-2509
[13]  
HUISGEN R, 1962, ANN, V563, P105
[14]  
ISIHARA H, 1966, NATURE, V210, P1222
[15]  
KHADEM HE, 1962, J CHEM SOC, P3155
[16]  
KHADEM HE, 1963, ADV CARBOHYD CHEM, V18, P99
[18]   PHOTOCHEMICAL DECOMPOSITION OF GEMINAL DIAZIDES .2. SOLUTION PHOTOLYSIS OF BENZOPHENONE DIAZIDE [J].
MORIARTY, RM ;
KLIEGMAN, JM .
JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 1967, 89 (23) :5959-&
[19]  
MORIARTY RM, 1967, J AM CHEM SOC, V89, P5958
[20]  
MULLIGAN TW, 1962, J ORG CHEM, V27, P4663