1,4-DIHYDRO-1,4-DIAZOCINE - N-SUBSTITUTION AND STRUCTURE (AROMATICITY)

被引:21
作者
BREUNINGER, M
GALLENKAMP, B
MULLER, KH
FRITZ, H
PRINZBACH, H
DALY, JJ
SCHONHOLZER, P
机构
[1] UNIV FREIBURG,LEHRSTUHL ORGAN CHEM,D-7800 FREIBURG,FED REP GER
[2] HOFFMANN LA ROCHE & CO AG,CH-4002 BASEL,SWITZERLAND
来源
ANGEWANDTE CHEMIE-INTERNATIONAL EDITION IN ENGLISH | 1979年 / 18卷 / 12期
关键词
D O I
10.1002/anie.197909641
中图分类号
O6 [化学];
学科分类号
0703 ;
摘要
Rings having 10 delocalizable electrons are of interest as potentially aromatic compounds. The unsubstituted 1,4‐dihydro‐1,4‐diazocine 1 has now been prepared by two independent syntheses. Some N,N′‐disubstituted derivatives of this ring system were already known. On the basis of its chemical behavior, spectra, and planar structure (confirmed by X‐ray structure analysis), 1 is to be regarded as a 10π aromatic species. No prototropic shift to give 2 or 3 is observed. The character of the N,N′‐disubstituted derivatives 4 is critically dependent upon the substituents. (Figure Presented.) Copyright © 1979 by Verlag Chemie, GmbH, Germany
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页码:964 / 965
页数:2
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[21]  
SCHWESINGER R, 1973, ANGEW CHEM, V85, P1107