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関連する概念動画

Hydroboration-Oxidation of Alkenes03:08

Hydroboration-Oxidation of Alkenes

10.8K
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.
10.8K
Alkylation of β-Diester Enolates: Malonic Ester Synthesis01:14

Alkylation of β-Diester Enolates: Malonic Ester Synthesis

4.0K
Malonic ester synthesis is a method to obtain α substituted carboxylic acids from ꞵ-diesters such as diethyl malonate and alkyl halides.
4.0K
Exceptions to the Octet Rule02:55

Exceptions to the Octet Rule

36.6K
Many covalent molecules have central atoms that do not have eight electrons in their Lewis structures. These molecules fall into three categories:
36.6K
Hybridization of Atomic Orbitals I03:24

Hybridization of Atomic Orbitals I

64.7K
The mathematical expression known as the wave function, ψ, contains information about each orbital and the wavelike properties of electrons in an isolated atom. When atoms are bound together in a molecule, the wave functions combine to produce new mathematical descriptions that have different shapes. This process of combining the wave functions for atomic orbitals is called hybridization and is mathematically accomplished by the linear combination of atomic orbitals. The new orbitals that...
64.7K
α-Bromination of Carboxylic Acids: Hell–Volhard–Zelinski Reaction01:15

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

3.6K
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...
3.6K
Regioselectivity and Stereochemistry of Hydroboration02:36

Regioselectivity and Stereochemistry of Hydroboration

9.3K
A significant aspect of hydroboration–oxidation is the regio- and stereochemical outcome of the reaction.
Hydroboration proceeds in a concerted fashion with the attack of borane on the π bond, giving a cyclic four-centered transition state. The –BH2 group is bonded to the less substituted carbon and –H to the more substituted carbon. The concerted nature requires the simultaneous addition of –H and –BH2 across the same face of the alkene giving syn stereochemistry.
9.3K

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関連する実験動画

Updated: Dec 28, 2025

Synthesis of a Borylated Ibuprofen Derivative Through Suzuki Cross-Coupling and Alkene Boracarboxylation Reactions
08:56

Synthesis of a Borylated Ibuprofen Derivative Through Suzuki Cross-Coupling and Alkene Boracarboxylation Reactions

Published on: November 30, 2022

3.3K

ボロナートエステルブルバレン

Harshal D Patel1, Thanh-Huyen Tran1, Christopher J Sumby1

  • 1Department of Chemistry , The University of Adelaide , Adelaide 5005 , SA , Australia.

Journal of the American Chemical Society
|February 12, 2020
PubMed
まとめ
この要約は機械生成です。

新しい方法は,ボロナートエステルブルヴァレンの簡単な合成を可能にします. これにより,スズキカップリングによる後期的な多様化が可能になり,制御された同位体分布を持つ様々な置換ブールバレンが生成されます.

さらに関連する動画

Regioselective O-Glycosylation of Nucleosides via the Temporary 2',3'-Diol Protection by a Boronic Ester for the Synthesis of Disaccharide Nucleosides
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Regioselective O-Glycosylation of Nucleosides via the Temporary 2',3'-Diol Protection by a Boronic Ester for the Synthesis of Disaccharide Nucleosides

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Metal-free Synthesis of Ynones from Acyl Chlorides and Potassium Alkynyltrifluoroborate Salts
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Metal-free Synthesis of Ynones from Acyl Chlorides and Potassium Alkynyltrifluoroborate Salts

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関連する実験動画

Last Updated: Dec 28, 2025

Synthesis of a Borylated Ibuprofen Derivative Through Suzuki Cross-Coupling and Alkene Boracarboxylation Reactions
08:56

Synthesis of a Borylated Ibuprofen Derivative Through Suzuki Cross-Coupling and Alkene Boracarboxylation Reactions

Published on: November 30, 2022

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Regioselective O-Glycosylation of Nucleosides via the Temporary 2',3'-Diol Protection by a Boronic Ester for the Synthesis of Disaccharide Nucleosides
08:46

Regioselective O-Glycosylation of Nucleosides via the Temporary 2',3'-Diol Protection by a Boronic Ester for the Synthesis of Disaccharide Nucleosides

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Metal-free Synthesis of Ynones from Acyl Chlorides and Potassium Alkynyltrifluoroborate Salts
09:58

Metal-free Synthesis of Ynones from Acyl Chlorides and Potassium Alkynyltrifluoroborate Salts

Published on: February 24, 2015

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科学分野:

  • 有機化学
  • 合成化学

背景:

  • ブルバレーンは,ダイナミックな構造を持つ高流動性分子である.
  • 代替ブルヴァレンの利用は 独特の性質を研究するために不可欠です

研究 の 目的:

  • 効率的な合成経路を開発し,ブルバレンエステル (Bullvalenes) をボロナートする.
  • ブルククジラを後期的に 多様化させるため
  • ブルヴァレンの同位体分布を制御する要因を調査する.

主な方法:

  • ボロナートエステルブルヴァレンの2〜4段階の合成手順の開発.
  • 多様化のためにスズキのクロスカップリング反応の適用.
  • プリプログラムされた代替装置のリンチピン戦略の利用
  • 溶液相同位体分布と単結晶X線構造の分析

主要な成果:

  • ボロナートエステルブルヴァレンは容易に合成される.
  • 単体,二体,三体置換ブールバレーンは,スズキカップリングでアクセスできます.
  • リンチピン戦略は,2つの異なる置換物の制御された導入を可能にします.
  • 結晶格子における同位体偏好は,一般的な形状選択性によって決定される.

結論:

  • 機能化されたブルヴァレンの効率的な合成アクセスは確立されています.
  • 遅い段階の多様化戦略は,複雑なブルバレーン・デリバティブに多岐にわたる経路を提供する.
  • 形状の選択性は,固体状態で観察された同位体分布を制御する.