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一种硝基-洪斯迪克尔反应:从不饱和羧酸到硝基苯乙烯和硝基芳烃。

A nitro-hunsdiecker reaction: from unsaturated carboxylic acids to nitrostyrenes and nitroarenes.

作者信息

Das Jaya Prakash, Sinha Pradipta, Roy Sujit

机构信息

Organometallics and Catalysis Laboratory, Chemistry Department, Indian Institute of Technology, Kharagpur 721302, India.

出版信息

Org Lett. 2002 Sep 5;4(18):3055-8. doi: 10.1021/ol0262901.

Abstract

[reaction: see text] The nitrodecarboxylation of aromatic alpha,beta-unsaturated carboxylic acids and ring-activated benzoic acids can be achieved using nitric acid (3 equiv) and catalytic AIBN (2 mol %) in MeCN. From the effect of various additives, the nitrodecarboxylation is postulated to involve the generation of an acyloxy radical RCO(2)() by a NO(3)() radical followed by attack of a NO(2)(*) radical.

摘要

[反应:见正文] 芳族α,β-不饱和羧酸和环活化苯甲酸的硝酰脱羧反应可通过在乙腈中使用硝酸(3当量)和催化量的偶氮二异丁腈(2摩尔%)来实现。根据各种添加剂的作用推测,硝酰脱羧反应涉及由硝酸根自由基(NO₃*)生成酰氧基自由基RCO₂*,随后亚硝酸根自由基(NO₂*)进行进攻。

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