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Generation and Trapping of Nitrosocarbonyl Intermediates
Chemical Reviews ( IF 62.1 ) Pub Date : 2017-01-20 00:00:00 , DOI: 10.1021/acs.chemrev.6b00684
Misal Giuseppe Memeo 1 , Paolo Quadrelli 1
Affiliation  

The nitrosocarbonyls (R–CONO) are highly reactive species and remarkable intermediates toward different synthetic targets. This review will cover a research area whose impact in current organic synthesis is constantly increasing in the chemical community. This review represents the first and comprehensive picture on the generation and trapping of nitrosocarbonyls and is solidly built on more than 380 papers. Six different classes of key starting materials such as hydroxamic acids, N-hydroxy carbamates, N-hydroxyureas, nitrile oxides, and 1,2,4-oxadiazole-4-oxides were highlighted. The content of the review surveys all the methods to generate the nitrosocarbonyls through different approaches (oxidative, thermal, photochemical, catalytic, aerobic, and the less common ones) in the light of efficiency, yields, and mildness. The most successful trapping agents employed to catch these fleeting intermediates are reviewed, exploiting their superior dienophilic, enophilic, and electrophilic power. The work is completed by paragraphs dedicated to the detection of the intermediates, theoretical studies, and insights about the challenges and future directions for the field.

中文翻译:

亚硝基羰基中间体的产生和诱捕

亚硝基羰基(R–CONO)是高反应性物种,是实现不同合成目标的重要中间体。这篇综述将涵盖一个研究领域,该领域对当前有机合成的影响在化学界不断增加。这篇综述代表了关于亚硝基羰基化合物的产生和捕集的第一张全面照片,它牢固地建立在380余篇论文上。六种不同的关键原料,例如异羟肟酸,N-羟基氨基甲酸酯,N突出显示了-羟基脲,一氧化氮和1,2,4-恶二唑-4-氧化物。审查的内容根据效率,产量和温和性,调查了通过不同方法(氧化,热,光化学,催化,好氧和较不常见的方法)生成亚硝基羰基的所有方法。综述了用于捕获这些短暂的中间体的最成功的捕集剂,它们利用了其优越的双亲,亲和和亲电能力。该工作由专门研究中间体的段落,理论研究以及对该领域的挑战和未来方向的见解所完成。
更新日期:2017-01-20
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