OXIDATION OF N-ACYLSULFILIMINES, N-SULFONYLSULFILIMINES, AND N-ARYLSULFILIMINES TO SULFOXIMINES BY META-CHLOROPEROXYBENZOATE ANION

被引：44

作者：

HUANG, SL

SWERN, D

机构：

[1] TEMPLE UNIV,FELS RES INST,PHILADELPHIA,PA 19122

[2] TEMPLE UNIV,DEPT CHEM,PHILADELPHIA,PA 19122

来源：

JOURNAL OF ORGANIC CHEMISTRY | 1979年 / 44卷 / 14期

关键词：

D O I：

10.1021/jo01328a039

中图分类号：

O62 [有机化学];

学科分类号：

070303 ; 081704 ;

摘要：

N-Acyl-, N-sulfonyl-, and N-arylsulfilimines are rapidly oxidized to the corresponding sulfoximines in high to virtually quantitative yields by m-chloroperoxybenzoate anion generated in situ in basic aqueous alcoholic media. In the one N-aryl case studied, S, S-dimethyl-N-(p-nitrophenyl)sulfilimine is converted unexpectedly to p-nitrosonitrobenzene in excellent yield by m-chloroperoxybenzoic acid but if the m-chloroperoxybenzoate anion is completely formed before sulfilimine is added, sulfoximine is obtained in over 90% yield. Reaction pathways are proposed. © 1979, American Chemical Society. All rights reserved.

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页码：2510 / 2513

页数：4

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