AROMATIC SOLVENT-INDUCED SHIFTS IN THE H-1-NMR SPECTRA OF NITRONES

被引:38
作者
AURICH, HG
FRANZKE, M
KESSELHEIM, HP
机构
[1] Fachbereich Chemie, University of Marburg, D-3550 Marburg, Hans-Meerwein-Straße
关键词
D O I
10.1016/S0040-4020(01)88126-6
中图分类号
O62 [有机化学];
学科分类号
070303 ; 081704 ;
摘要
In the H-1-NMR spectra of model compounds 1-3 in hexadeuteriobenzene the signals of protons at the E-side of the nitrone group are more extensively shifted to higher field by the effect of the aromatic solvent than the signals of protons at the Z-side. Utilizing this effect the existence of usual C,N-dialkylnitrones in the Z-form was confirmed. C-Acylnitrones as 8 and 9, however, exist in both of the isomeric forms, the equilibrium being strongly influenced by the solvent.
引用
收藏
页码:663 / 668
页数:6
相关论文
共 11 条
[1]   INTRAMOLECULAR CYCLOADDITION OF NITRONES [J].
AURICH, HG ;
BOUTAHAR, M ;
KOSTER, H ;
MOBUS, KD ;
RUIZ, L .
CHEMISCHE BERICHTE, 1990, 123 (10) :1999-2014
[2]   STERIC EFFECTS ON REGIOSELECTIVITY IN 1.3-DIPOLAR CYCLOADDITION OF C,N-DIALKYL NITRONES WITH ACCEPTOR-SUBSTITUTED ALKYNES [J].
AURICH, HG ;
FRANZKE, M ;
KESSELHEIM, HP ;
ROHR, M .
TETRAHEDRON, 1992, 48 (04) :669-682
[3]   DYNAMIC STEREOCHEMISTRY OF IMINES AND DERIVATIVES .11. SYNTHESIS AND STEREOCHEMISTRY OF (E)-NITRONE AND (Z)-NITRONE [J].
BJORGO, J ;
BOYD, DR ;
NEILL, DC ;
JENNINGS, WB .
JOURNAL OF THE CHEMICAL SOCIETY-PERKIN TRANSACTIONS 1, 1977, (03) :254-259
[4]   NITRONES AND OXAZIRIDINES .20. INTRA-MOLECULAR NITRONE 1,3-DIPOLAR CYCLOADDITION BY SUBSTITUENT INTERACTION - SYNTHESIS AND REDUCTION OF SOME TETRAHYDROPYRROLOISOXAZOLES [J].
BLACK, DSC ;
CROZIER, RF ;
RAE, ID .
AUSTRALIAN JOURNAL OF CHEMISTRY, 1978, 31 (09) :2013-2022
[5]  
BREUER E, 1989, NITRONES NITRONATES, P149
[6]   REACTIONS AT HIGH-PRESSURES - [3+2] DIPOLAR CYCLOADDITION OF NITRONES WITH VINYL ETHERS [J].
DICKEN, CM ;
DESHONG, P .
JOURNAL OF ORGANIC CHEMISTRY, 1982, 47 (11) :2047-2051
[7]   H-1 AND C-13 NMR-SPECTRA OF SEVERAL (E)-ALDONITRONES AND (Z)-ALDONITRONES [J].
INOUYE, Y ;
TAKAYA, K ;
KAKISAWA, H .
MAGNETIC RESONANCE IN CHEMISTRY, 1985, 23 (02) :101-103
[8]   STRUCTURAL STUDIES BY NUCLEAR MAGNETIC RESONANCE .19. N,N-DIMETHYLHYDRAZONES AND GENERAL COMMENTS ON CONFIGURATIONAL AND CONFORMATIONAL ISOMERISM [J].
KARABATSOS, GJ ;
TALLER, RA .
TETRAHEDRON, 1968, 24 (10) :3923-+
[9]   NMR-SPECTROSCOPIC CONFIGURATIONAL ASSIGNMENT OF ALDONITRONES [J].
KLEINPETER, E ;
MASCHMEIER, CP ;
KRAHNSTOVER, J ;
MATSCHINER, H ;
KOHLER, H .
JOURNAL FUR PRAKTISCHE CHEMIE, 1990, 332 (02) :261-264
[10]  
Torssell K. B. G., 1988, NITRILE OXIDES NITRO, P75