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Thermal and Photochemical Electrocyclic Reactions: Overview01:26

Thermal and Photochemical Electrocyclic Reactions: Overview

2.5K
Electrocyclic reactions are reversible reactions. They involve an intramolecular cyclization or ring-opening of a conjugated polyene. Shown below are two examples of electrocyclic reactions. In the first reaction, the formation of the cyclic product is favored. In contrast, in the second reaction, ring-opening is favored due to the high ring strain associated with cyclobutene formation.
2.5K
Olefin Metathesis Polymerization: Ring-Opening Metathesis Polymerization (ROMP)01:16

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

2.7K
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...
2.7K
Cycloaddition Reactions: MO Requirements for Photochemical Activation01:12

Cycloaddition Reactions: MO Requirements for Photochemical Activation

2.2K
Some cycloaddition reactions are activated by heat, while others are initiated by light. For example, a [2 + 2] cycloaddition between two ethylene molecules occurs only in the presence of light. It is photochemically allowed but thermally forbidden.
2.2K
Photochemical Electrocyclic Reactions: Stereochemistry01:26

Photochemical Electrocyclic Reactions: Stereochemistry

1.9K
The absorption of UV–visible light by conjugated systems causes the promotion of an electron from the ground state to the excited state. Consequently, photochemical electrocyclic reactions proceed via the excited-state HOMO rather than the ground-state HOMO. Since the ground- and excited-state HOMOs have different symmetries, the stereochemical outcome of electrocyclic reactions depends on the mode of activation; i.e., thermal or photochemical.
Selection Rules: Photochemical Activation
1.9K
Cycloaddition Reactions: Overview01:16

Cycloaddition Reactions: Overview

2.9K
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.
2.9K
Cationic Chain-Growth Polymerization: Mechanism00:57

Cationic Chain-Growth Polymerization: Mechanism

2.4K
The cationic polymerization mechanism consists of three steps: initiation, propagation, and termination. In the initiation step of the polymerization process, the π bond of a monomer gets protonated by the Lewis acid catalyst, which is formed from boron trifluoride and water. The protonation of the π bond generates a carbocation stabilized by the electron‐donating group. In the propagation step, the π bond of the second monomer acts as a nucleophile and attacks the...
2.4K

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Updated: Sep 28, 2025

Depolymerizable Olefinic Polymers Based on Fused-Ring Cyclooctene Monomers
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Depolymerizable Olefinic Polymers Based on Fused-Ring Cyclooctene Monomers

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プログラムされたポリエネサイクル 染色体破壊によって可能

Megan M Solans1, Vitalii S Basistyi1, James A Law1

  • 1Department of Chemistry and Biochemistry, Florida State University, Tallahassee, Florida 32306, United States.

Journal of the American Chemical Society
|April 4, 2022
PubMed
まとめ
この要約は機械生成です。

研究者はβ-イオニル誘導体を用いた新しいポリエネサイクリング戦略を開発した. この方法は複雑な [4.4.1]-プロペランを効率的に合成し,地域選択性を改善し,天然製品のための新しい合成経路を可能にします.

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[DPEPhosbcpCu]PF6: A General and Broadly Applicable Copper-Based Photoredox Catalyst
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[DPEPhosbcpCu]PF6: A General and Broadly Applicable Copper-Based Photoredox Catalyst

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Cercosporin-Photocatalyzed [4+1]- and [4+2]-Annulations of Azoalkenes Under Mild Conditions
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Cercosporin-Photocatalyzed [4+1]- and [4+2]-Annulations of Azoalkenes Under Mild Conditions

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Depolymerizable Olefinic Polymers Based on Fused-Ring Cyclooctene Monomers
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[DPEPhosbcpCu]PF6: A General and Broadly Applicable Copper-Based Photoredox Catalyst
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[DPEPhosbcpCu]PF6: A General and Broadly Applicable Copper-Based Photoredox Catalyst

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Cercosporin-Photocatalyzed [4+1]- and [4+2]-Annulations of Azoalkenes Under Mild Conditions
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Cercosporin-Photocatalyzed [4+1]- and [4+2]-Annulations of Azoalkenes Under Mild Conditions

Published on: July 17, 2020

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科学分野:

  • 有機化学
  • 合成化学
  • 自然製品合成

背景:

  • ポリエネサイクリングは天然製品合成の重要な戦略です.
  • 既存の生体模倣戦術は 地域選択性が限られていることが多い.
  • [4.4.1]-プロペランのような複雑なポリサイクリック・スキャファッドへのアクセスは依然として困難です.

研究 の 目的:

  • 新しい地域選択型ポリエネサイクリング戦略を開発する.
  • [4.4.1]プロペランを合成し,効率と基板の範囲を向上させる.
  • 自然製品の合成における新しい戦略の有用性を実証する.

主な方法:

  • β-イオニル誘導体を利用する新しいポリエネサイクリング戦略の開発.
  • 光誘導による解結合を用いて対熱力学的ポリエンを生成する.
  • [4.4.1]-プロペランの形成のためにヘック・バイサイクリングを使用する.

主要な成果:

  • 新しいカスケード戦略では,既存の方法と比較して,地域選択性が向上しています.
  • このアプローチは,電子が豊富で,電子が欠けている (ヘテロ) アリル基の幅広い範囲を許容する.
  • タクソジオンとサルヴィアスペラノールの完全な合成が成功していることが実証された.

結論:

  • 開発された戦略は, [4.4.1]-プロペランへの強力な新しい経路を提供します.
  • この方法は,以前の戦術の地域選択性と基質範囲の制限を克服します.
  • このアプローチにより,以前は入手不可能な同位体アビエタン・ディターペンが得られます.