合成了一种新型,高度对称的双氧桥接化合物
Faiz Ahmed Khan1, Jyotirmayee Dash
1Department of Chemistry, Indian Institute of Technology, Kanpur-208 016, India.
Journal of the American Chemical Society
|March 14, 2002
概括
一种新型的五环双桥化合物被有效地合成使用易于获得的原料. 这三步方法提供了一种通用途径,以应力氧桥式衍生品.
科学领域:
- 有机化学 有机化学
- 合成化学 合成化学
- 药用化学 医学化学
背景情况:
- 具有双氧桥架结构的新型五环化合物对有机合成感兴趣.
- 有效的合成路径到复杂的多环分子是非常受欢迎的.
研究的目的:
- 开发一种新型五环双氧桥合化合物的高效三步合成方法.
- 为了证明开发的方法合成相关的应变氧桥衍生物的多功能性.
主要方法:
- 合成始于四-5,5-二甲基cyclopentadiene和1,4-环xadiene.
- 一种2:1双添加物的催化氧化,然后进行一转化.
- 通过化,获得最终的五环双氧桥合化合物.
主要成果:
- 一种新的五环双桥化合物 (化合物8) 用显著的效率进行了合成.
- 三步合成的整体收益率为29.1%.
- 该方法成功地应用于其他诺博尼尔α-二基,产生了相应的应变氧桥衍生物.
结论:
- 已经建立了一个简单而有效的三步合成策略,用于新型五环双氧桥合化合物.
- 开发的方法提供了一种通用的方法,用于访问紧张的氧桥分子架构.
- 这项工作为聚环化合物合成领域做出了宝贵的贡献.
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Overview
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...
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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α,β-Unsaturated carbonyl compounds are molecules bearing a carbonyl and alkene functionality in conjugation with each other. The conjugation in the molecule leads to three resonance structures. The hybrid form exhibits two probable electrophilic sites: the carbonyl carbon and the β carbon.
C–C Bond Formation: Aldol Condensation Overview
Aldol condensation is an important route in synthetic organic chemistry used to generate a new carbon–carbon bond under basic or acidic conditions. The aldol condensation reaction presented in Figure 1 constitutes an aldol addition reaction followed by the dehydration process.
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Crossed aldol addition is the reaction between two different carbonyl compounds under acidic or basic conditions. Here, both the carbonyl compounds function as nucleophiles and electrophiles. As shown in Figure 1, such a reaction yields a mixture of products, two of which are formed via self-condensation, while the remaining two are formed via crossed-condensation. Without adjustment, the reaction's usefulness in organic chemistry is decreased.
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