STUDIES ON AZOLE-TO-AZOLE INTERCONVERSIONS - SUBSTITUENT EFFECTS ON THE RING-DEGENERATE EQUILIBRATION BETWEEN 3-AROYLAMINO-5-METHYL-1,2,4-OXADIAZOLES AND 3-ACETYLAMINO-5-ARYL-1,2,4-OXADIAZOLES

被引：18
|
作者：
BUSCEMI, S
FRENNA, V
VIVONA, N
PETRILLO, G
SPINELLI, D
机构：
[1] CNR,CTR STUDIO CHIM COMPOSTI CICLOALIFATICI & AROMATI,I-16132 GENOA,ITALY
[2] UNIV BOLOGNA,DIPARTIMENTO CHIM ORGAN A MANGINI,I-40127 BOLOGNA,ITALY
来源：
TETRAHEDRON | 1995年 / 51卷 / 17期
关键词：
D O I：
10.1016/0040-4020(95)98709-Q
中图分类号：
O62 [有机化学];
学科分类号：
070303 ; 081704 ;
摘要：
The title reaction has been studied both in CD3OD and (t)BuOK/CD3OD by means of H-1 NMR measurements. The equilibrium composition and the effect exerted thereon by X-substituents in the aryl moiety have been found to be quite different whether neutral or anionic forms are involved. In the first case the effect of X is meagre and 3-acetylamino-5-aryl-1,2,4-oxadiazoles are more stable than the 3-aroylamino-5-methyl isomers. Vice-versa, when anions are involved the substituent effect is remarcable and the equilibrium can be, for strongly electron-withdrawing X-groups, even largely shifted towards the anions of the 3-aroylamino-5-methyl-1,2,4-oxadiazoles.
引用
收藏
页码：5133 / 5142
页数：10
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