Hydrodediazoniation of dry arenediazonium o-benzenedisulfonimides with hydrogen peroxide

被引：20

作者：

Barbero, M ^{[1
]}

Degani, I ^{[1
]}

Dughera, S ^{[1
]}

Fochi, R ^{[1
]}

机构：

[1] Univ Turin, Dipartimento Chim Gen & Organ Applicata, I-10125 Turin, Italy

来源：

SYNTHESIS-STUTTGART | 2004年 / 14期

关键词：

reductions; diazonium compounds; radical reactions; sulfur;

D O I：

10.1055/s-2004-831183

中图分类号：

O62 [有机化学];

学科分类号：

070303 ; 081704 ;

摘要：

This report describes the hydrodediazoniation of dry arenediazonium o-benzenedisulfonimides 1 with hydrogen peroxide (2) in THF at reflux. The new procedure is general, giving positive results in the presence of both electron-donating and electron-withdrawing substituents. Furthermore, it does not suffer from steric effects and always gives the pure reduction products 3 in excellent yields (15 examples, average yield = 93%). All the reactions show over 90% recovery of o-benzenedisulfonimide (4) that can be reused to prepare the salts 1. The collateral proofs we performed led us to hypothesize, for this reaction, a free-radical chain mechanism in which 2 is the exclusive; hydrogen source in the arenes Ar-H3.

引用

页码：2386 / 2390

页数：5

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