Reactivity of 3-N-(4-chloro-3-nitrophenyl)-sydnone in SNAr reactions

被引:0
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作者
Braz, VR
Echevarria, A
Miller, J
机构
[1] UNIV FED PARAIBA,LTF,BR-58051970 JOAO PESSOA,PARAIBA,BRAZIL
[2] UNIV FED PARAIBA,DEPT QUIM,BR-58051970 JOAO PESSOA,PARAIBA,BRAZIL
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中图分类号
O62 [有机化学];
学科分类号
070303 ; 081704 ;
摘要
We have made a kinetic study of the nucleophilic substitution reactions of 3-N-(4-chloro-3-nitrophenyl)sydnone with methoxide ion in methanol:acetone (80:20 v/v) and with piperidine in the same solvent and DMF. These data have been compared with relevant data for the reactions of these nucleophiles with 2-(4-chloro-3-nitrophenyl)-1,3-diphenyl-1,3,4-triazolium-2-thiolate and with 1-chloro-2,4-dinitrobenzene. The special character of a mesoionic system as a substituent in SNAr reactions, due to the marked separation of positive and negative regions, was clearly evident with the sydnone system. The solvent effects have been analysed.
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页码:507 / 511
页数:5
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