STRUCTURAL EFFECTS ON THE ISOINDOLE-ISOINDOLENINE EQUILIBRIUM - SUBSTITUTION IN THE PYRRYL RING

被引:17
作者
CHACKO, E [1 ]
BORNSTEIN, J [1 ]
SARDELLA, DJ [1 ]
机构
[1] BOSTON COLL,DEPT CHEM,CHESTNUT HILL,MA 02167
关键词
D O I
10.1016/S0040-4020(01)93722-6
中图分类号
O62 [有机化学];
学科分类号
070303 ; 081704 ;
摘要
The influence of substitution in the pyrryl ring on the isoindole-isoindolenine equilibrium has been studied by NMR spectroscopy. Electron-releasing groups selectively stabilize the isoindolenine tautomer in which the substituent is conjugated with the π-system, while electron-withdrawing groups have the opposite effect. However, sequential introduction of identical groups into the 1- and 3-positions leads, first to a shift of the equilibrium in one direction, then to a shift in opposite direction. Reasons for this behavior are discussed. © 1979.
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页码:1055 / 1058
页数:4
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