Oxidation of hydrazones by hypervalent organoiodine reagents: Regeneration of the carbonyl group and facile syntheses of alpha-acetoxy and alpha-alkoxy azo compounds

被引：45

作者：

Barton, DHR ^{[1
]}

Jaszberenyi, JC ^{[1
]}

Liu, WS ^{[1
]}

Shinada, T ^{[1
]}

机构：

[1] TECH UNIV BUDAPEST,RES GRP,HUNGARIAN ACAD SCI,DEPT ORGAN CHEM TECHNOL,H-1111 BUDAPEST,HUNGARY

来源：

TETRAHEDRON | 1996年 / 52卷 / 47期

关键词：

D O I：

10.1016/0040-4020(96)00940-4

中图分类号：

O62 [有机化学];

学科分类号：

070303 ; 081704 ;

摘要：

Various hydrazone derivatives of alpha-keto esters were prepared. The carbonyl group was readily regenerated in high yield from phenylhydrazones through oxidative hydrolysis using hypervalent organoiodine(III) reagents-either bis(trifluoroacetoxy)-iodobenzene (BTIB) in aqueous acetonitrile or hydroxy (tosyloxy)iodobenzene (HTIB) in chloroform, alpha-Acetoxy phenyl- or methylazo compounds were readily synthesized by oxidation of the corresponding hydrazones with iodobenzene diacetate (IBDA) in dichloromethane or acetic acid. alpha-Methoxy phenyl- or methylazo compounds were also prepared by oxidation of the hydrazones in methanol. The mechanisms of the oxidation reactions are discussed. Copyright (C) 1996 Elsevier Science Ltd

引用

页码：14673 / 14688

页数：16

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