氧化方法可以有效地获得循环亚
Martin S Maier1,2, Katharina Hüll1,2, Martin Reynders1,2
1Department of Chemistry and Center for Integrated Protein Science (CIPSM) , Ludwig Maximilian University Munich , 81377 Munich , Germany.
Journal of the American Chemical Society
|October 5, 2019
概括
现在可以用合成方法获得. 一种新的氧化循环化方法使得用于各种应用的功能化diazocines的快速,克级合成成为可能.
科学领域:
- 有机化学
- 摄影化学
- 材料科学
背景情况:
- 阿佐是光药学和材料科学中使用的关键光开关.
- 一个较新的类型 - - 循环二氧化具有独特的特性,但面临着合成的局限性.
研究的目的:
- 开发一种通用,高产的合成协议,以获取多种功能循环diazocines.
- 探索替代剂对二氧化的光异构化和热放松的影响.
主要方法:
- 迪亚尼林的氧化循环.
- 模块化基板合成用于多种功能化.
- 循环亚素的格拉姆尺度合成
主要成果:
- 建立了一个强大的合成功能循环diazocines的协议.
- 系统地研究了替代剂对光异构和热放松的影响.
- 该方法促进了一种新型的九个成员循环亚博的合成.
结论:
- 开发的方法显著提高了循环二素的合成可用性.
- 这项工作为将二氧化纳入各种功能分子铺平了道路.
- 这些发现揭示了素作为先进的可光切换材料的潜力.
相关概念视频
Reactions at the Benzylic Position: Oxidation and Reduction
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The benzylic position describes the position of a carbon atom attached directly to a benzene ring. Benzene by itself does not undergo oxidation. In contrast, the benzylic carbon is quite reactive in the presence of strong oxidizing agents such as KMnO4 or H2CrO4. Therefore, alkylbenzenes are readily oxidized to benzoic acid, irrespective of the type of alkyl groups.
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Oxidation of Alkenes: Anti Dihydroxylation with Peroxy Acids
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Diols are compounds with two hydroxyl groups. In addition to syn dihydroxylation, diols can also be synthesized through the process of anti dihydroxylation. The process involves treating an alkene with a peroxycarboxylic acid to form an epoxide. Epoxides are highly strained three-membered rings with oxygen and two carbons occupying the corners of an equilateral triangle. This step is followed by ring-opening of the epoxide in the presence of an aqueous acid to give a trans diol.
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Preparation of Epoxides
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Overview
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Epoxidation of alkenes via oxidation with peroxy acids involves the conversion of a carbon–carbon double bond to an epoxide using the oxidizing agent meta-chloroperoxybenzoic acid, commonly known as MCPBA. Since the O–O bond of peroxy acids is very weak, the addition of electrophilic oxygen of peroxy acids to...
Epoxides result from alkene oxidation, which can be achieved by a) air, b) peroxy acids, c) hypochlorous acids, and d) halohydrin cyclization.
Epoxidation with Peroxy Acids
Epoxidation of alkenes via oxidation with peroxy acids involves the conversion of a carbon–carbon double bond to an epoxide using the oxidizing agent meta-chloroperoxybenzoic acid, commonly known as MCPBA. Since the O–O bond of peroxy acids is very weak, the addition of electrophilic oxygen of peroxy acids to...
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Oxidation of Alkenes: Syn Dihydroxylation with Osmium Tetraoxide
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Alkenes are converted to 1,2-diols or glycols through a process called dihydroxylation. It involves the addition of two hydroxyl groups across the double bond with two different stereochemical approaches, namely anti and syn. Dihydroxylation using osmium tetroxide progresses with syn stereochemistry.
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Oxidative Cleavage of Alkenes: Ozonolysis
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In ozonolysis, ozone is used to cleave a carbon–carbon double bond to form aldehydes and ketones, or carboxylic acids, depending on the work-up.
Ozone is a symmetrical bent molecule stabilized by a resonance structure.
Ozone is a symmetrical bent molecule stabilized by a resonance structure.
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Cycloaddition Reactions: Overview
3.3K
Cycloadditions are one of the most valuable and effective synthesis routes to form cyclic compounds. These are concerted pericyclic reactions between two unsaturated compounds resulting in a cyclic product with two new σ bonds formed at the expense of π bonds. The [4 + 2] cycloaddition, known as the Diels–Alder reaction, is the most common. The other example is a [2 + 2] cycloaddition.
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