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

页码：1623 / 1630

页数：8

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