PERISELECTIVITY BETWEEN THE [1,4] AND [3,3] THERMAL SIGMATROPIC REARRANGEMENTS OF 2-ALLYLOXYPYRIDINE N-OXIDES

被引：12
|
作者：
ALKER, D [1 ]
OLLIS, WD [1 ]
SHAHRIARIZAVAREH, H [1 ]
机构：
[1] UNIV SHEFFIELD, DEPT CHEM, SHEFFIELD S3 7HF, S YORKSHIRE, ENGLAND
来源：
JOURNAL OF THE CHEMICAL SOCIETY-PERKIN TRANSACTIONS 1 | 1990年 / 06期
关键词：
D O I：
10.1039/p19900001623
中图分类号：
O62 [有机化学];
学科分类号：
070303 ; 081704 ;
摘要：
Thermal rearrangement of 2-allyloxypyridine N-oxides (4a-c) yields N-allyloxy-2-pyridones (5a-c) and 3-allyl-N-hydroxy-2-pyridones (6a-c). These transformations are shown to be regiospecific and on this basis it is proposed that the reactions involve concerted [1,4] and [3,3] sigmatropic rearrangements. Supporting evidence based on solvent effects, temperature effects, and substituent effects is given.
引用
收藏
页码：1623 / 1630
页数：8
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