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无金属、室温、酸-KSO介导的烯烃硝化方法:一种合成硝基烯烃的简便方法。

Metal-free, room temperature, acid-KSO mediated method for the nitration of olefins: an easy approach for the synthesis of nitroolefins.

作者信息

Ambala Srinivas, Singh Rohit, Singh Maninder, Cham Pankaj Singh, Gupta Ria, Munagala Gurunadham, Yempalla Kushalava Reddy, Vishwakarma Ram A, Singh Parvinder Pal

机构信息

Medicinal Chemistry Division, CSIR-Indian Institute of Integrative Medicine India

Academy of Scientific and Innovative Research India.

出版信息

RSC Adv. 2019 Sep 25;9(52):30428-30431. doi: 10.1039/c9ra06414a. eCollection 2019 Sep 23.

Abstract

Here, we have developed a simple, room temperature method for the nitration of olefins by using inexpensive sodium nitrite as a source of nitro groups in the presence of trifluoroacetic acid (TFA) and potassium persulfate (KSO) under an open atmosphere. Styrenes and mono-substituted olefins give stereo-selective corresponding -nitroolefins under optimized conditions, however, 1,1-bisubstituted olefins give a mixture of - and -nitroolefins. The optimized conditions work well with electron-donating, electron-withdrawing, un-substituted and heterocyclic styrenes and mono-substituted olefins and give corresponding nitroolefins with good to excellent yields.

摘要

在此,我们开发了一种简单的室温方法,用于烯烃的硝化反应。该方法在开放气氛下,以廉价的亚硝酸钠作为硝基源,在三氟乙酸(TFA)和过硫酸钾(KSO)存在下进行。在优化条件下,苯乙烯和单取代烯烃可立体选择性地生成相应的β-硝基烯烃,然而,1,1-二取代烯烃会生成β-和γ-硝基烯烃的混合物。优化条件对供电子、吸电子、未取代和杂环苯乙烯以及单取代烯烃均适用,并能以良好至优异的产率生成相应的硝基烯烃。

https://cdn.ncbi.nlm.nih.gov/pmc/blobs/f670/9072150/a80e364cbeeb/c9ra06414a-f1.jpg

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