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相关概念视频

Aldehydes and Ketones to Alkenes: Wittig Reaction Mechanism01:14

Aldehydes and Ketones to Alkenes: Wittig Reaction Mechanism

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The Wittig reaction, which converts aldehydes or ketones to alkenes using phosphorus ylides, proceeds through a nucleophilic addition‒elimination process.
The reaction begins with the nucleophilic addition between a phosphorus ylide and the carbonyl compound. Due to its carbanionic character,  phosphorus ylide acts as a strong nucleophile and attacks the electrophilic carbonyl group. This generates a charge-separated dipolar intermediate called betaine. The negatively charged oxygen atom and...
4.1K
Aldehydes and Ketones to Alkenes: Wittig Reaction Overview01:19

Aldehydes and Ketones to Alkenes: Wittig Reaction Overview

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The Wittig reaction is the conversion of carbonyl compounds-aldehydes and ketones-to alkenes using phosphorus ylides, or the Wittig reagent. The reaction was pioneered by Prof. Georg Wittig, for which he was awarded the Nobel Prize in Chemistry.
8.4K
α-Bromination of Carboxylic Acids: Hell–Volhard–Zelinski Reaction01:15

α-Bromination of Carboxylic Acids: Hell–Volhard–Zelinski Reaction

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The method to achieve α-brominated carboxylic acids using a mixture of phosphorus tribromide and bromine is known as the Hell–Volhard–Zelinski reaction. The reaction is catalyzed by phosphorus tribromide, which can be used directly or produced in situ from red phosphorus and bromine. The mechanism comprises PBr3 catalyzed conversion of acid to acid bromide and hydrogen bromide. The acid bromide enolizes to its enol form in the presence of HBr. The nucleophilic enol attacks the...
3.3K
Hydroboration-Oxidation of Alkenes03:08

Hydroboration-Oxidation of Alkenes

9.4K
In addition to the oxymercuration–demercuration method, which converts the alkenes to alcohols with Markovnikov orientation, a complementary hydroboration-oxidation method yields the anti-Markovnikov product. The hydroboration reaction, discovered in 1959 by H.C. Brown, involves the addition of a B–H bond of borane to an alkene giving an organoborane intermediate. The oxidation of this intermediate with basic hydrogen peroxide forms an alcohol.
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Preparation of Alcohols via Addition Reactions02:15

Preparation of Alcohols via Addition Reactions

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Overview
The acid-catalyzed addition of water to the double bond of alkenes is a large-scale industrial method used to synthesize low-molecular-weight alcohols. An acidic atmosphere is required to allow the hydrogen in the water molecule to act as an electrophile and attack the double bond in an alkene. The addition of a proton to the double bond creates a carbocation intermediate. The proton preferentially bonds to the less substituted end of the double bond to create a more stable carbocation...
6.7K
The Phosphorus Cycle01:21

The Phosphorus Cycle

41.4K
Unlike carbon, water, and nitrogen, phosphorus is not present in the atmosphere as a gas. Instead, most phosphorus in the ecosystem exists as compounds, such as phosphate ions (PO43-), found in soil, water, sediment and rocks. Phosphorus is often a limiting nutrient (i.e., in short supply). Consequently, phosphorus is added to most agricultural fertilizers, which can cause environmental problems related to runoff in aquatic ecosystems.
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相关实验视频

Updated: Oct 22, 2025

Preparation and Reactivity of a Triphosphenium Bromide Salt: A Convenient and Stable Source of PhosphorusI
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Preparation and Reactivity of a Triphosphenium Bromide Salt: A Convenient and Stable Source of PhosphorusI

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- 玻拉 - 维蒂格反应

Andryj M Borys1, Ella F Rice1, Gary S Nichol1

  • 1EaStCHEM School of Chemistry, University of Edinburgh, Joseph Black Building, David Brewster Road, Edinburgh EH9 3FJ, United Kingdom.

Journal of the American Chemical Society
|August 26, 2021
PubMed
概括

一种新型的酸-博拉-维蒂格反应可以使用易于获得的碳化合物直接合成酸. 这种方法类似于经典的维蒂格反应,在有机化学中提供了新的合成途径.

科学领域:

  • 有机化学
  • 合成有机化学
  • 主要组化学

背景情况:

  • 经典的维蒂格反应是合成碳化合物的基石.
  • 基的类相似物是有价值的合成中间体,但它们的制备可能具有挑战性.
  • 过渡性酸代表一种具有新型结合形成潜力的反应性物种.

研究的目的:

  • 开发一种用于直接制备基的新合成途径.
  • 探索过渡性酸与碳化合物的反应性.
  • 调查新型波拉-维蒂格反应和经典的维蒂格反应之间的机制相似之处.

主要方法:

  • 过渡性博烯 (Mes*PB-NR2) 与各种碳化合物 (甲基化物,子,,胺) 的反应.
  • 介质1,2,3-氧乙的分离和表征
  • 用热或易斯酸促进的中间体循环反转产生基.
  • 实验研究和密度函数理论 (DFT) 计算以阐明反应机制.

主要成果:

  • 酸-博拉-维蒂格反应成功地从各种碳酸基质中产生酸.
  • 过渡性酸与碳化合物反应形成1,2,3-酸,类似于维蒂格氧酸.
  • 这些中间体的循环逆转提供了可行的基路径.

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Mizoroki-Heck Cross-coupling Reactions Catalyzed by Dichloro{bis[1,1',1''-phosphinetriyltripiperidine]}palladium Under Mild Reaction Conditions
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Mizoroki-Heck Cross-coupling Reactions Catalyzed by Dichloro{bis[1,1',1''-phosphinetriyltripiperidine]}palladium Under Mild Reaction Conditions

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Preparation and Use of Carbonyl-decorated Carbenes in the Activation of White Phosphorus
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Preparation and Use of Carbonyl-decorated Carbenes in the Activation of White Phosphorus

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Mizoroki-Heck Cross-coupling Reactions Catalyzed by Dichloro{bis[1,1',1''-phosphinetriyltripiperidine]}palladium Under Mild Reaction Conditions
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Mizoroki-Heck Cross-coupling Reactions Catalyzed by Dichloro{bis[1,1',1''-phosphinetriyltripiperidine]}palladium Under Mild Reaction Conditions

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  • DFT研究和实验数据证实了与经典维蒂格反应的显著机理相似性.
  • 结论:

    • 酸-博拉-维蒂格反应为合成酸提供了一种直接且多用途的方法.
    • 反应通过1,2,3-甲中间体进行,反映了维蒂格机制.
    • 这项工作扩大了酸的合成效用,并为基于的化反应提供了新的见解.