JoVE - Journal of Visualized Experiments
JoVE Visualize
Contact Us
このページは機械翻訳されています。他のページは英語で表示される場合があります。 View in English

バイオクロブタン挿入によるチオフェンのダイオロマティブリング拡張

  • 0Organisch-Chemisches Institut, Westfälische Wilhelms-Universität Münster (WWU), 48149 Münster, Germany.
Clinical Neuroscience (new York, N.y.) +

|

2023年7月6日

|

2023年7月6日

PubMedで要約を見る

まとめ

この要約は機械生成です。

研究者は合成化学で 骨格の輪を拡大する新しい方法を開発しました この光誘導反応は,穏やかな条件下でチオフェンとビサイクロ[1.1.0]ブタンから8つの環を効率的に生成します.

科学分野

  • 合成有機化学
  • 写真化学
  • ヘテロサイクル化学

背景

  • 骨格環の拡大は有機合成における重要な変化です.
  • 特に小環挿入によるヘテロサイクリック膨張の効率的な方法は限られている.
  • 複雑なサイクルシステムを構築するための新しい戦略の開発は,重要な関心事である.

研究 の 目的

  • 新しく発光された 芳香の輪の拡大反応を報告する
  • チオフェンリングにビサイクロ[1.1.0]ブタンを挿入する.
  • 温和な環境で8つの環を合成する.

主な方法

  • フォトレドックス触媒を用いた光誘導反応.
  • ビサイクロ[1.1.0]ブタンがチオフェン誘導体にデオロマティブに挿入される
  • 合成の有用性を評価するための範囲評価と製品誘導.
  • 反応メカニズムを解明するための計算研究.

主要な成果

  • ティオフェン環の膨張による8基のバイサイクル環の合成に成功した.
  • 幅広い機能群の適合性と優れた化学的および地域選択性を示した.
  • フォトレドックス誘発の 変異経路を特定した
  • 製品には重要な合成価値とさらなる派生の可能性がありました.

結論

  • 開発された方法は,複合的な8つ構成のバイサイクルの化合物への効率的な経路を提供します.
  • 反応は穏やかな条件下で進行し,様々な機能群と互換性があります.
  • この発見は,ヘテロサイクル環の膨張のための光還元触媒に関する新しい洞察を提供します.

関連する概念動画

Olefin Metathesis Polymerization: Ring-Opening Metathesis Polymerization (ROMP) 01:16

2.6K

Ring-opening metathesis polymerization or ROMP involves strained cycloalkenes as starting materials. The mechanism of ROMP proceeds by reacting cycloalkene with Grubbs catalyst to give metallacyclobutane intermediate which undergoes a ring-opening reaction to form new carbene. The new carbene reacts with another molecule of cycloalkene. Repetition of these steps leads to the formation of an unsaturated open-chain polymer product. All these steps are reversible, however, relieving the ring...

Cycloaddition Reactions: Overview 01:16

2.6K

Cycloadditions are one of the most valuable and effective synthesis routes to form cyclic compounds. These are concerted pericyclic reactions between two unsaturated compounds resulting in a cyclic product with two new σ bonds formed at the expense of π bonds. The [4 + 2] cycloaddition, known as the Diels–Alder reaction, is the most common. The other example is a [2 + 2] cycloaddition.

The feasibility of cycloaddition reactions under thermal and photochemical conditions can be...

Diels–Alder Reaction Forming Bridged Bicyclic Products: Stereochemistry 01:29

4.7K

Diels–Alder reactions between cyclic dienes locked in an s-cis configuration and dienophiles yield bridged bicyclic products.

Dienophiles with one or more electron-withdrawing substituents form stereochemically different products in which the substituents are oriented in an endo (towards) or exo (away) configuration relative to the double bond.

The endo isomer is formed faster and is the kinetic product. The exo isomer is more stable and is the thermodynamic...

Cycloaddition Reactions: MO Requirements for Thermal Activation 01:16

3.6K

Thermal cycloadditions are reactions where the source of activation energy needed to initiate the reaction is provided in the form of heat. A typical example of a thermally-allowed cycloaddition is the Diels–Alder reaction, which is a [4 + 2] cycloaddition. In contrast, a [2 + 2] cycloaddition is thermally forbidden.

The reaction occurs between the highest occupied molecular orbital (HOMO) of one π component and the lowest unoccupied molecular orbital (LUMO) of the other. These are...

[4+2] Cycloaddition of Conjugated Dienes: Diels–Alder Reaction 01:16

10.3K

The Diels–Alder reaction is an example of a thermal pericyclic reaction between a conjugated diene and an alkene or alkyne, commonly referred to as a dienophile. The reaction involves a concerted movement of six π electrons, four from the diene and two from the dienophile, forming an unsaturated six-membered ring. As a result, these reactions are classified as [4+2] cycloadditions.

From a molecular orbital perspective, the interacting lobes of the two π systems must be in phase...

Electrophilic 1,2- and 1,4-Addition of X<sub>2</sub> to 1,3-Butadiene 01:14

2.5K

Electrophilic addition of halogens to alkenes proceeds via a cyclic halonium ion to form a 1,2-dihalide or a vicinal dihalide.

Conjugated dienes react with halogens in a similar manner. However, in addition to the 1,2-dihalide, they also form a 1,4-dihalide. The mechanism involves two steps.
First, a nucleophilic attack by one of the diene π bonds on the electrophilic center of the polarized halogen molecule forms a halonium ion intermediate. This is followed by a nucleophilic attack of...