Transition from p Radicals to s Radicals: Substituent-Tuned Cyclization of Hydrazonyl Radicals

被引：95

作者：

Duan, Xiao-Yong ^{[1
,2
]}

Zhou, Neng-Neng ^{[1
,2
]}

Fang, Ran ^{[1
,2
]}

Yang, Xiu-Long ^{[1
,2
]}

Yu, Wei ^{[1
,2
]}

Han, Bing ^{[1
,2
]}

机构：

[1] Lanzhou Univ, State Key Lab Appl Organ Chem, Lanzhou 730000, Peoples R China

[2] Lanzhou Univ, Coll Chem & Chem Engn, Lanzhou 730000, Peoples R China

来源：

ANGEWANDTE CHEMIE-INTERNATIONAL EDITION | 2014年 / 53卷 / 12期

基金：

中国国家自然科学基金;

关键词：

alkenes; cyclization; heterocycles; radicals; synthetic methods; ELECTRON-SPIN RESONANCE; AZOMETHINE IMINES; ALKENES; GENERATION; CONSTRUCTION; PYRAZOLINES; DIAMINATION; OXIDATION; NUCLEUS; OXIMES;

D O I：

10.1002/anie.201309918

中图分类号：

O6 [化学];

学科分类号：

0703 ;

摘要：

Hydrazonyl radicals are known for their -electronic structures; however, their sigma-electronic structures have not been reported as yet. Herein, we show that readily accessible ,- and ,-unsaturated N-trichloroacetyl and N-trifluoroacetyl hydrazones can be conveniently converted into hydrazonyl sigma radicals, which subsequently undergo 5-exo-trig radical cyclization at the N-1 or N-2 atom to form pyrazolines and azomethine imines, respectively.

引用

页码：3158 / 3162

页数：5

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[3]

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