Formation of o-nitrosobenzaldehyde from hydrolysis of o-nitrobenzyl tosylate. Evidence of intramolecular nucleophilic interaction

被引：20

作者：

Chen, LJ ^{[1
]}

Burka, LT ^{[1
]}

机构：

[1] NIEHS, Res Triangle Pk, NC 27709 USA

来源：

TETRAHEDRON LETTERS | 1998年 / 39卷 / 30期

关键词：

D O I：

10.1016/S0040-4039(98)01068-5

中图分类号：

O62 [有机化学];

学科分类号：

070303 ; 081704 ;

摘要：

Hydrolysis of o-nitrobenzyl tosylate in CH3CN:H2O (1:1, v/v) gave o-nitrobenzyl alcohol and o-nitrosobenzaldehyde in 1.8 : 1 ratio. Formation of o-nitrosobenzaldehyde indicates that the nitro group participates in the leaving of the tosylate group. o-Nitrosobenzaldehyde was reduced by biological thiols to give o-aminobenzaldehyde. Reaction of o-nitrosobenzaldehyde with 1 mol of benzylamine afforded 3-(N-benzylamino)anthranil (or its tautomer) as a major product. Published by Elsevier Science Ltd.

引用

页码：5351 / 5354

页数：4

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