MILD OXIDATION OF ALKYL-HALIDES

被引：13

作者：

BERGERON, RJ

HOFFMAN, PG

机构：

[1] Department of Pharmaceutical Chemistry, J. Hillis Miller Health Center, University of Florida, Gainesville

来源：

JOURNAL OF ORGANIC CHEMISTRY | 1979年 / 44卷 / 11期

关键词：

D O I：

10.1021/jo01325a019

中图分类号：

O62 [有机化学];

学科分类号：

070303 ; 081704 ;

摘要：

The application of N-phenyltrifluoromethanesulfonamide to the oxidation of activated halides (α-halo carbonyl compounds) has been extended and shown to be general. A new reagent, N-(4-acetoxyphenyl)trifluoromethanesul-fonamide, has been developed for the mild oxidation of unactivated alkyl halides. The reagent was N-alkylated with a number of different alkyl halides. The elements of CF3SO2H were then eliminated under mild basic conditions generating imines which were easily hydrolyzed to the corresponding amines and carbonyl compounds. The ease of CF3SO2-elimination was demonstrated to be dependent on intermediate aminoquinone formation. © 1979, American Chemical Society. All rights reserved.

引用

页码：1835 / 1839

页数：5

共 17 条

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