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Radical Substitution: Allylic Bromination01:27

Radical Substitution: Allylic Bromination

5.7K
In organic synthesis, the formation of products can be altered by changing the reaction conditions. For example, a dibromo addition product is formed when propene is treated with bromine at room temperature. In contrast, propene undergoes allylic substitution in non-polar solvents at high temperatures to give 3-bromopropene. In order to avoid the addition reaction, the bromine concentration must be kept as low as possible throughout the reaction. This can be achieved using N-bromosuccinimide...
5.7K
Radical Substitution: Allylic Chlorination01:31

Radical Substitution: Allylic Chlorination

2.6K
Typically, when alkenes react with halogens at low temperatures, an addition reaction occurs. However, upon increasing the temperature or under reaction conditions that form radicals, providing a low but steady concentration of halogen radicals, allylic substitution reaction is favored. This is because allylic hydrogens are very reactive as the formed intermediate is resonance stabilized. For example, when propene is treated with chlorine in the gas phase at 400 °C, it undergoes allylic...
2.6K
π Molecular Orbitals of the Allyl Cation and Anion01:18

π Molecular Orbitals of the Allyl Cation and Anion

4.8K
An allyl group is a three-carbon conjugated system where the sp³-hybridized allylic carbon is bonded to a CH=CH2 group via a single bond. Allyl anions can be obtained by treating propene with a strong base that can deprotonate methyl groups. Allyl cations are formed as intermediates during substitution reactions involving allylic halides. In both cases, the hybridization of the allylic carbon changes from sp3 to sp2, giving rise to a carbon chain with three sp2-hybridized carbons, each with...
4.8K
Preparation of Amines: Alkylation of Ammonia and Amines01:30

Preparation of Amines: Alkylation of Ammonia and Amines

3.8K
Alkylation is one of the methods used to prepare amines. Direct alkylation of ammonia or a primary amine with an alkyl halide gives polyalkylated amines along with a quaternary ammonium salt through successive SN2 reactions. This process of making the quaternary salt through the direct alkylation method is called exhaustive alkylation.
Each alkylation step makes the nitrogen center more nucleophilic, which triggers successive alkylations until a quaternary ammonium salt is formed. Considering...
3.8K
Amines to Alkenes: Hofmann Elimination01:16

Amines to Alkenes: Hofmann Elimination

2.7K
Alkenes can be obtained from amines via an E2 elimination. The amine is first converted into a good leaving group, such as a quaternary ammonium salt. This is accomplished by treating the amine with an excess of alkyl halide, which results in a halide salt. Next, the halide salt is transformed into a hydroxide salt that functions as a base to enable elimination.
Under thermal conditions, the hydroxide can abstract a proton from the β carbon; this generates an alkene with the simultaneous...
2.7K
Amines to Amides: Acylation of Amines01:19

Amines to Amides: Acylation of Amines

2.8K
Various carboxylic acid derivatives (such as acid chlorides, esters, and anhydrides) can be used for the acylation of amines to yield amides. The reaction requires two equivalents of amines. The first amine molecule functions as a nucleophile and attacks the carbonyl carbon to produce a tetrahedral intermediate. This is followed by the loss of the leaving group and restoration of the C=O bond.
Next, the second equivalent of amine serves as a Brønsted base and deprotonates the quaternary...
2.8K

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関連する実験動画

Updated: Oct 20, 2025

Facile Preparation of 2Z,4E-Dienamides by the Olefination of Electron-deficient Alkenes with Allyl Acetate
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Facile Preparation of 2Z,4E-Dienamides by the Olefination of Electron-deficient Alkenes with Allyl Acetate

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遅い段階の分子間アリルC-Hアミネーション

Takafumi Ide1, Kaibo Feng1, Charlie F Dixon1

  • 1Department of Chemistry, Roger Adams Laboratory, University of Illinois, 505 South Mathews Avenue, Urbana, Illinois 61801, United States.

Journal of the American Chemical Society
|September 13, 2021
PubMed
まとめ

この研究では,複雑な分子の選択的後期アリルアミネーションのためのマンガン触媒を導入します. この突破により,天然製品に窒素を効率的に導入でき,その生物学的活性が潜在的に変化します.

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A Two-Step Protocol for Umpolung Functionalization of Ketones Via Enolonium Species
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A Microwave-Assisted Direct Heteroarylation of Ketones Using Transition Metal Catalysis
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A Microwave-Assisted Direct Heteroarylation of Ketones Using Transition Metal Catalysis

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Facile Preparation of 2Z,4E-Dienamides by the Olefination of Electron-deficient Alkenes with Allyl Acetate
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Facile Preparation of 2Z,4E-Dienamides by the Olefination of Electron-deficient Alkenes with Allyl Acetate

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A Two-Step Protocol for Umpolung Functionalization of Ketones Via Enolonium Species
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A Microwave-Assisted Direct Heteroarylation of Ketones Using Transition Metal Catalysis
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科学分野:

  • 有機化学
  • カタリシス
  • 自然製品合成

背景:

  • アリルC-H機能化は天然製品を改造するための鍵です.
  • 分子間アリルアミネーションは,反応性と選択性において課題に直面し,基板の範囲を制限する.

研究 の 目的:

  • 分子間アリルC-Hアミネーションのための選択的で効率的な方法を開発する.
  • 自然製品を含む多種多様な複雑な有機分子の機能化を可能にします.

主な方法:

  • 持続可能なマンガネスパークロロフタロシアニン触媒 ([MnIII(ClPc)) を利用した.
  • 競合する機能群を含む32のサイクルおよび線形化合物のアミネーションを調査した.
  • 触媒の選択性を理解するためにメカニズム研究を行いました.

主要な成果:

  • 様々な基板で選択的,準備的な分子間アリルC-Hアミネーションを達成した.
  • 自然製品の後期機能化において,高いサイト,地域,およびダイアステレオ選択性 (> 20: 1) を示した.
  • 段階的なメカニズムとともに,電離性で大容量な性質が選択性に寄与する.

結論:

  • [MnIII(ClPc) ]触媒は,アリルアミネーション反応に挑戦するための堅固な解決策を提供します.
  • この方法は,自然製品と複雑な分子のための遅い段階の機能化戦略を大幅に前進させます.
  • 触媒の選択性は,合成化学におけるアリルアミネーションの適用範囲を拡大する.