Investigation of the transition-metal- and acid-catalyzed reactions of β-(N-tosyl)amino diazo carbonyl compounds

被引：70

作者：

Jiang, N ^{[1
]}

Ma, ZH ^{[1
]}

Qu, ZH ^{[1
]}

Xing, XY ^{[1
]}

Xie, LF ^{[1
]}

Wang, JB ^{[1
]}

机构：

[1] Peking Univ, Coll Chem, Dept Biol Chem, Minist Educ,Key Lab Bioorgan Chem & Mol Engn, Beijing 100871, Peoples R China

来源：

JOURNAL OF ORGANIC CHEMISTRY | 2003年 / 68卷 / 03期

关键词：

D O I：

10.1021/jo0259818

中图分类号：

O62 [有机化学];

学科分类号：

070303 ; 081704 ;

摘要：

A series of beta-(N-tosyl)amino diazo carbonyl compounds have been prepared by nucleophilic condensation of N-tosylimines with acyldiazomethanes. The diazo decomposition of these diazo carbonyl compounds under various catalytic conditions, including Rh(II) carboxylates, Cu(I) and Cu(II) complexes, PhCO2Ag/Et3N, TsOH, and SnCl2.2H(2)O, has been investigated. It was found that, in most cases, the diazo decomposition gave preferentially 1,2-aryl migration product, but 1,2-hydride migration predominated when PhCO2Ag/Et3N was the catalytic system. Hammett correlation has been applied in the analysis of the electronic effects of 1,2-aryl migration. The factors that govern the migratory preference and the mechanistic aspects of the reaction are discussed.

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页码：893 / 900

页数：8

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