ASSISTANCE OF N,N-DISUBSTITUTED AMIDOXIMES IN CYCLODEHYDROGENATION REACTIONS

被引:0
作者
MOHRLE, H
LESSEL, J
机构
来源
ZEITSCHRIFT FUR NATURFORSCHUNG SECTION B-A JOURNAL OF CHEMICAL SCIENCES | 1992年 / 47卷 / 09期
关键词
DEHYDROGENATION WITH HG-EDTA COMPLEX; AMIDOXIMES; NITRONES; QUINAZOLINE; 3-OXIDES;
D O I
暂无
中图分类号
O61 [无机化学];
学科分类号
070301 ; 081704 ;
摘要
o-(tert-Amino)benzamidoximes 6, N,N-disubstituted at the amid-N-atom of the nucleophilic moiety, are suitable neighbouring groups in cyclodehydrogenation reactions of tertiary amines using mercury(II)-edta. The kind of the N-substituents and the amount of oxidizing agent control the nature of the products, lactams 9 and anellated nitrones 8. The configuration of the tricyclic systems is determined by NMR spectroscopic methods. During the reaction an inversion of the configuration of the oxime moiety occurs, which is explained by an electrocyclic mechanism.
引用
收藏
页码:1333 / 1340
页数:8
相关论文
共 18 条
[1]  
BOHLMANN F, 1958, CHEM BER, V91, P2172
[2]  
CRABB TA, 1984, ADV HETEROCYCLIC CHE, V36, P9
[3]  
DIGNAM KJ, 1977, J CHEM SOC PERK T 2, P1457, DOI 10.1039/p29770001457
[4]   REACTIVITY OF 1,3-DIPOLES IN AQUEOUS-SOLUTION .4. KINETICS AND MECHANISM OF ISOMERIZATION OF AMIDOXIMES IN AQUEOUS-SOLUTION [J].
DIGNAM, KJ ;
HEGARTY, AF .
JOURNAL OF THE CHEMICAL SOCIETY-PERKIN TRANSACTIONS 2, 1979, (10) :1437-1443
[5]   AMIDOXIMES - DETERMINATION OF CONFIGURATION AND STUDY OF Z-E ISOMERIZATION MECHANISM [J].
GOZLAN, H ;
MICHELOT, R ;
RICHE, C ;
RIPS, R .
TETRAHEDRON, 1977, 33 (19) :2535-2542
[6]  
HAMER J, 1964, CHEM REV, V64, P490
[7]   1.3-DIPOLARE CYCLOADDITIONEN - RUCKSCHAU UND AUSBLICK [J].
HUISGEN, R .
ANGEWANDTE CHEMIE-INTERNATIONAL EDITION, 1963, 75 (13) :604-+
[8]  
Huisgen R., 1963, ANGEW CHEM INT EDIT, P565, DOI [10.1002/anie.196305651, DOI 10.1002/ANIE.196305651]
[9]  
KANEKO C, 1967, TETRAHEDRON LETT, P5237
[10]   MASS-SPECTRA OF NITRONES AND THE ISOMERIC OXIME O-ETHERS [J].
KOSTYANOVSKII, RG ;
PLESHKOVA, AP ;
VOZNESENSKII, VN ;
MISHCHENKO, AI ;
PROSYANIK, AV ;
MARKOV, VI .
BULLETIN OF THE ACADEMY OF SCIENCES OF THE USSR DIVISION OF CHEMICAL SCIENCE, 1980, 29 (02) :240-246