Search research articles

お問い合わせ

JoVEについて

概要リーダーシップブログ JoVEヘルプセンター

著者向け

出版プロセス編集委員会範囲と方針査読よくある質問投稿

図書館員向け

推薦の声購読アクセスリソース図書館諮問委員会よくある質問

研究

JoVE Journal Methods Collections JoVE Encyclopedia of Experiments アーカイブ

教育

JoVE Core JoVE Business JoVE Science Education JoVE Lab Manual 教員リソースセンター教員サイト

プライバシーポリシー

関連する概念動画

Base-Catalyzed Ring-Opening of Epoxides

Base-Catalyzed Ring-Opening of Epoxides

Due to their highly strained structures, epoxides can readily undergo ring-opening reactions through nucleophilic substitution, either in the presence of an acid or a base. The nucleophilic substitution reactions in the presence of acid are called acid-catalyzed ring-opening reactions, and nucleophilic substitution reactions in the presence of a base are called base-catalyzed ring-opening reactions. Epoxides undergo base-catalyzed ring-opening reactions in the presence of a strong nucleophile...

Acid-Catalyzed Ring-Opening of Epoxides

Acid-Catalyzed Ring-Opening of Epoxides

Epoxides that are three-membered ring systems are more reactive than other cyclic and acyclic ethers. The high reactivity of epoxides originates from the strain present in the ring. This ring strain acts as a driving force for epoxides to undergo ring-opening reactions either with halogen acids or weak nucleophiles in the presence of mild acid. The acid catalyst converts the epoxide oxygen, a poor leaving group, into an oxonium ion, a better leaving group, making the reaction feasible. The...

Regioselectivity and Stereochemistry of Acid-Catalyzed Hydration

Regioselectivity and Stereochemistry of Acid-Catalyzed Hydration

The rate of acid-catalyzed hydration of alkenes depends on the alkene's structure, as the presence of alkyl substituents at the double bond can significantly influence the rate.

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

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

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...

ortho–para-Directing Activators: –CH3, –OH, –&NoBreak;NH2, –OCH3

ortho–para-Directing Activators: –CH₃, –OH, –⁠NH₂, –OCH₃

All ortho–para directors, excluding halogens, are activating groups. These groups donate electrons to the ring, making the ring carbons electron-rich. Consequently, the reactivity of the aromatic ring towards electrophilic substitution increases. For instance, the nitration of anisole is about 10,000 times faster than the nitration of benzene. The electron-donating effect of the methoxy group in anisole activates the ortho and para positions on the ring and stabilizes the corresponding...

Thermal Electrocyclic Reactions: Stereochemistry

Thermal Electrocyclic Reactions: Stereochemistry

The stereochemistry of electrocyclic reactions is strongly influenced by the orbital symmetry of the polyene HOMO. Under thermal conditions, the reaction proceeds via the ground-state HOMO.
Selection Rules: Thermal Activation
Conjugated systems containing an even number of π-electron pairs undergo a conrotatory ring closure. For example, thermal electrocyclization of (2E,4E)-2,4-hexadiene, a conjugated diene containing two π-electron pairs, gives trans-3,4-dimethylcyclobutene.

こちらも読む

関連記事

共著者、ジャーナル、引用グラフによってこの研究に関連する記事。

並び替え

Same author

Aloin suppresses cancer cell growth via autophagy-promoted NEDD8 de-NEDDylation to target GPX4 for ferroptosis induction.

Bioorganic chemistry·2026

Same author

Sex-specific associations between prenatal PM<sub>2.5</sub> exposure and reproductive hormone levels in offspring aged 1-2 years: A prospective birth cohort study.

Environmental research·2026

Same author

Robust SWCNT-OH/GO membranes for scalable recovery of moxifloxacin from high-salinity organic wastewater.

Nature communications·2026

Same author

Interfacial Active-Oxygen Transport in Inverse CuO<sub><i>x</i></sub>/Perovskite Catalysts for Low-Temperature CO Oxidation.

ACS applied materials & interfaces·2026

Same author

Interpretable spatial multi-omics data integration and dimensionality reduction with SpaMV.

Nature communications·2026

Same author

Determining Quantum Mechanical Methods Suitable for Quantitative Modeling of Hydrogen Atom Transfer by Halogen Atoms.

Journal of chemical theory and computation·2026

Same journal

Switching Site Selectivity in Alkoxyamine Hydration: From Lone-Pair Direction to Solvent Network Dominance.

Journal of the American Chemical Society·2026

Same journal

A Topotactic Leap: 2D Layers to 3D Large-Pore Zeolite.

Journal of the American Chemical Society·2026

Same journal

Enhanced Hydrogen Evolution over Single-Atom Catalysts via Electrostatic Polarization in Contact-electro-catalysis.

Journal of the American Chemical Society·2026

Same journal

Tumor Acidity-Activatable Ionizable Lipid Nanoparticles for Selective Oncolytic Therapy.

Journal of the American Chemical Society·2026

Same journal

Alternating Magnetic Field Promotes Ammonia Cracking by Disrupting the Sabatier Limitation of Ruthenium Catalytic Species.

Journal of the American Chemical Society·2026

Same journal

Bulk Ferromagnetic Icosahedral Quasicrystals without Rapid Quenching.

Journal of the American Chemical Society·2026

関連記事をすべて見る

Search research articles

関連する実験動画

Updated: Jun 27, 2025

Photogeneration of N-Heterocyclic Carbenes: Application in Photoinduced Ring-Opening Metathesis Polymerization

Photogeneration of N-Heterocyclic Carbenes: Application in Photoinduced Ring-Opening Metathesis Polymerization

Published on: November 29, 2018

カーベンの補助によるアレーンリング開封

Zengrui Cheng¹, Haoran Xu², Zhibin Hu¹

¹State Key Laboratory of Natural and Biomimetic Drugs, School of Pharmaceutical Sciences, Peking University, 100191 Beijing, China.

Journal of the American Chemical Society

|May 1, 2024

まとめ

この要約は機械生成です。

研究者は,アリルアジドを多重結合エニンに変換する新しいカルベンの支援戦略を開発した. この突破は合成を簡素化し炭酸塩化学の応用を広げました

さらに関連する動画

Preparation of Contiguous Bisaziridines for Regioselective Ring-Opening Reactions

Preparation of Contiguous Bisaziridines for Regioselective Ring-Opening Reactions

Published on: July 28, 2022

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

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

Published on: June 21, 2017

関連する実験動画

Last Updated: Jun 27, 2025

Photogeneration of N-Heterocyclic Carbenes: Application in Photoinduced Ring-Opening Metathesis Polymerization

Photogeneration of N-Heterocyclic Carbenes: Application in Photoinduced Ring-Opening Metathesis Polymerization

Published on: November 29, 2018

Preparation of Contiguous Bisaziridines for Regioselective Ring-Opening Reactions

Preparation of Contiguous Bisaziridines for Regioselective Ring-Opening Reactions

Published on: July 28, 2022

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

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

Published on: June 21, 2017

科学分野:

有機化学
合成化学
キャタリシス

背景:

アレンのデオロマイゼーションとC-H機能化は進んでいるが,アレンのリング開きは依然として困難である.
アロマティック化合物の高い結合解離と共振エネルギーは,リング開き反応を阻害する.

研究の目的:

効率的なアレンリング開封のための新しいカーベンの支援戦略を導入する.
バルクアレン化学物質から付加価値の多重結合連鎖分子の合成を可能にします.
アリルアジドから多重結合エニンへの簡素化された経路を提供する.

主な方法:

カルベンの補助反応によるアレン環開封の開発
反応メカニズムを解明するための密度関数理論 (DFT) の計算.
複雑な分子と溶融リングシステムの後期的な修飾への方法の適用.

主要な成果:

カルベンの助力による新しいリング開封戦略を実証した.
様々なアリルアジド系を価値ある多重結合エニンに変換した.
多段階の前駆体とクロスカップリング反応を避け,単純な条件下で合成を達成した.
DFT計算でメカニズムを検証し,広範な適用の可能性を強調しました.

結論:

カルベンの支援による戦略は,アレン・リング開通の新たな経路を提供します.
この方法は,多重結合エニンの合成を簡素化し,従来のアプローチの限界を克服する.
この発見は,複合結合分子合成におけるアレンの使用を刺激すると予想される.