REVERSE COPE ELIMINATION-REACTIONS .1. MECHANISM AND SCOPE

被引：64

作者：

CIGANEK, E ^{[1
]}

READ, JM ^{[1
]}

CALABRESE, JC ^{[1
]}

机构：

[1] DUPONT MERCK PHARMACEUT CO,EXPTL STN,CENT RES & DEV,WILMINGTON,DE 19880

来源：

JOURNAL OF ORGANIC CHEMISTRY | 1995年 / 60卷 / 18期

关键词：

D O I：

10.1021/jo00123a013

中图分类号：

O62 [有机化学];

学科分类号：

070303 ; 081704 ;

摘要：

N-4-Pentenyl- and N-5-hexenyl-N-methylhydroxylamine cyclized under mild conditions in a reverse Cope elimination reaction to give 1,2-dimethylpyrrolidine N-oxide and 1,2-dimethylpiperidine N-oxide, respectively. The reaction was shown to be concerted and thermodynamically controlled. The scope of this novel cyclization is discussed, and comparisons are made with the closely related and previously reported cyclization of monosubstituted alkenylhydroxylamines to give cyclic hydroxylamines.

引用

页码：5795 / 5802

页数：8

共 27 条

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