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関連する概念動画

Aldehydes and Ketones to Alkenes: Wittig Reaction Mechanism01:14

Aldehydes and Ketones to Alkenes: Wittig Reaction Mechanism

4.1K
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

8.4K
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

3.3K
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.
9.4K
Preparation of Alcohols via Addition Reactions02:15

Preparation of Alcohols via Addition Reactions

6.7K
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.
41.4K

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関連する実験動画

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

Published on: November 22, 2016

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フォスファ-ボラ-ウィティグ反応

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
まとめ

新しいフォスファ-ボラ-ウィティグ反応は,容易に入手可能なカルボニル化合物を用いて,直接のフォスファルケンの合成を可能にします. この方法は,古典的なウィティグ反応に並行して,有機リン化学における新しい合成経路を提供します.

科学分野:

  • オルガノフォスファース化学
  • 合成有機化学
  • メイングループ 化学

背景:

  • クラシックなウィティグ反応は,カルボニル化合物からアルケンを合成するための基石である.
  • アルケンのフォスファルケンは,価値ある合成中間物質ですが,その準備は困難です.
  • トランジエントフォスファボレンは,新しい結合形成の可能性のある反応性種のクラスを表します.

研究 の 目的:

  • フォスファルケンの直接製剤のための新しい合成経路を開発する.
  • カーボニル化合物との一時的なフォスファボレンの反応性を調査する.
  • 新しいフォスファ・ボラ・ウィチグ反応と古典的なウィチグ反応のメカニズム的な類似性を調査する.

主な方法:

  • トランジエントフォスファボレン (Mes*PB-NR2) と様々なカルボニル化合物 (アルデヒド,ケトン,エステル,アミド) の反応
  • 1,2,3-フォスファボラオキセタンの分離と特徴付け
  • 熱またはルイス酸が促進した中間物質のサイクロレバーションにより,フォスファルケーンが得られる.
  • 実験的研究と密度関数理論 (DFT) の計算により,反応メカニズムが解明される.

主要な成果:

さらに関連する動画

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

Published on: March 20, 2014

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関連する実験動画

Last 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

Published on: November 22, 2016

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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

Published on: October 3, 2014

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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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  • フォスファ-ボラ-ウィティグ反応は,様々なカルボニル基板からフォスファルケンを成功裏に生成する.
  • 暫定的なホスファボレンは,カルボニル化合物と反応して1,2,3-ホスファボラオキセタンを形成し,ウィチグのオキシホスフェタンに類似する.
  • これらの中間物質のサイクロレバーションは,フォスファルケーンへの有効な経路を提供します.
  • DFTの研究と実験データは,古典的なウィティグ反応と有意なメカニズム的類似性を確認しています.
  • 結論:

    • フォスファ-ボラ-ウィティグ反応は,フォスファルケンを合成するための直接的かつ多用途な方法を提供します.
    • 反応は1,2,3-ホスファボラオキセタン中間体を通して進行し,ウィティグのメカニズムを反映している.
    • この研究は,フォスファボレンの合成有用性を拡大し,リン基のオレフィネーション反応に関する新しい洞察を提供します.