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质子催化氧-联:形成2-氧乙
Nandita M Weliange1, Endre Szuromi, Paul R Sharp
1125 Chemistry, University of Missouri-Columbia, Columbia, Missouri 65211, USA.
Journal of the American Chemical Society
|June 10, 2009
概括
一个氧复合物促进了从一个氧复合物和norbornene中形成2-platinaoxetane. 这种反应机制对于理解瓦克尔氧化过程至关重要.
科学领域:
- 有机金属化学 有机金属化学
- 催化剂是一种催化剂.
背景情况:
- 瓦克尔氧化是一个重要的工业过程,用于将基因转化为化物或.
- 了解催化氧化氧化的详细机制对于过程优化至关重要.
研究的目的:
- 研究氧复合物在氧乙中间体的形成中的作用.
- 提供对瓦克尔烯氧化反应的机械洞察力.
主要方法:
- 一个oxo复合体与norbornene在氧复合体的存在下发生反应.
- 反应中间体的表征,包括质子化二氧乙.
主要成果:
- 氧复合物 (5) 从氧复合物 (1) 和norbornene (NB) 中调解形成2-platinaoxetane (2).
- 氧复合物 (5) 和诺波 (NB) 之间的轻易反应产生质子化2-氧乙烯 (7).
结论:
- 氧乙中间体的形成是由氧复合物调解的支持.
- 这些发现提供了证据,证明这些氧乙途径参与了瓦克尔烯氧化机制.
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01:46Oxidative Cleavage of Alkenes: Ozonolysis
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.
03:00Preparation of Epoxides
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...
02:04Oxidation of Alkenes: Anti Dihydroxylation with Peroxy Acids
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.
02:44Oxidation of Alkenes: Syn Dihydroxylation with Osmium Tetraoxide
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.
01:27Vicinal Diols via Reductive Coupling of Aldehydes or Ketones: Pinacol Coupling Overview
Wilhelm Rudolph Fittig discovered the pinacol coupling reaction in 1859. It is a radical dimerization reaction and involves the reductive coupling of aldehydes or ketones in the presence of hydrocarbon solvent to yield vicinal diols.
02:36Oxymercuration-Reduction of Alkenes
Oxymercuration–reduction of alkenes is one of the major reactions converting alkenes to alcohols. It involves the hydration of alkenes with mercuric acetate in a mixture of tetrahydrofuran and water, forming an organomercury adduct. This is followed by a demercuration step in which the adduct is reduced to an alcohol using sodium borohydride.