A selective cleavage of aromatic benzyl ethers located ortho to a carbonyl group by magnesium bromide.

被引：33

作者：

Haraldsson, GG ^{[1
]}

Baldwin, JE ^{[1
]}

机构：

[1] DYSON PERRINS LAB,OXFORD OX1 3QY,ENGLAND

来源：

TETRAHEDRON | 1997年 / 53卷 / 01期

关键词：

D O I：

10.1016/S0040-4020(96)00964-7

中图分类号：

O62 [有机化学];

学科分类号：

070303 ; 081704 ;

摘要：

The selective debenzylation of various aromatic dibenzyloxy aldehydes by magnesium bromide in anhydrous ether-benzene solution by a gentle reflux for 36 hours is described. Only benzyloxy groups located ortho to the carbonyl group were cleaved cleanly and highly efficiently, leaving other benzyl ether groups unaffected. A six-membered chelation ring intermediate is proposed. The preparation of all relevant dibenzyloxy napthalene and benzene aldehyde precursors is described by benzylation of the corresponding diols and usually, a subsequent Vilsmeier formylation. Copyright (C) 1996 Elsevier Science Ltd

引用

页码：215 / 224

页数：10

共 14 条

[1]

ASKLEY V, 1962, J CHEM SOC, P1260

[2] THE SELECTIVE CLEAVAGE OF AROMATIC BENZYL ETHERS WITH MAGNESIUM BROMIDE VIA NEIGHBORING GROUP EFFECT [J].