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Aromatic Hydrocarbon Cations: Structural Overview01:18

Aromatic Hydrocarbon Cations: Structural Overview

Cycloheptatriene is a neutral monocyclic unsaturated hydrocarbon that consists of an odd number of carbon atoms and an intervening sp3 carbon in the ring. The three double bonds in the ring correspond to 6 π electrons, which is a Huckel number, and therefore satisfies the criteria of 4n + 2 π electrons. However, the intervening sp3 carbon disrupts the continuous overlap of p orbitals. As a result, cycloheptatriene is not aromatic.
Removing one hydrogen from the intervening CH2 group with both...
Cycloalkanes02:28

Cycloalkanes

Cycloalkanes are saturated cyclic hydrocarbons with carbon atoms arranged in the form of rings. They have two fewer hydrogen atoms than the corresponding acyclic alkane; therefore, their general formula is CnH2n. The structural formulas of cycloalkanes are simplified using the line-angle representation. The regular polygons are used to represent the cycloalkane rings, with each side representing a carbon-carbon bond.
The IUPAC nomenclature of cycloalkanes follows similar rules that apply to...
Reduction of Benzene to Cyclohexane: Catalytic Hydrogenation01:28

Reduction of Benzene to Cyclohexane: Catalytic Hydrogenation

Unlike the easy catalytic hydrogenation of an alkene double bond, hydrogenation of a benzene double bond under similar reaction conditions does not take place easily. For example, in the reduction of stilbene, the benzene ring remains unaffected while the alkene bond gets reduced. Hydrogenation of an alkene double bond is exothermic and a favorable process. In contrast, to hydrogenate the first unsaturated bond of benzene, an energy input is needed; that is, the process is endothermic. This is...
Alkynes to Aldehydes and Ketones: Hydroboration-Oxidation02:47

Alkynes to Aldehydes and Ketones: Hydroboration-Oxidation

Introduction
One of the convenient methods for the preparation of aldehydes and ketones is via hydration of alkynes. Hydroboration-oxidation of alkynes is an indirect hydration reaction in which an alkyne is treated with borane followed by oxidation with alkaline peroxide to form an enol that rapidly converts into an aldehyde or a ketone. Terminal alkynes form aldehydes, whereas internal alkynes give ketones as the final product.
Aldehydes and Ketones with HCN: Cyanohydrin Formation Overview01:32

Aldehydes and Ketones with HCN: Cyanohydrin Formation Overview

Cyanohydrins are compounds that contain –CN and –OH groups on the same carbon atom. They are formed by the nucleophilic addition of the cyanide ions to the carbonyl group. Cyanide ions are highly basic and nucleophilic and can be generated from HCN under aqueous conditions. However, since HCN is a weak acid, the number of cyanide ions generated is very small. Hence, a small amount of base or KCN/NaCN is added to HCN to increase the concentration of the cyanide ions in the reaction mixture.
Carbocations02:10

Carbocations

Carbocations are one of the reaction intermediates formed during several nucleophilic substitutions or elimination reactions. A carbocation is an electron-deficient species with the central carbon atom having six electrons and three bonded atoms. The central carbon in a carbocation is sp2 hybridized with trigonal planar geometry. It has an empty p orbital perpendicular to the plane of the structure that can accept electrons. Thus, carbocations act as strong electrophiles and may react with any...

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Updated: May 30, 2026

Synthesis of Antiviral Tetrahydrocarbazole Derivatives by Photochemical and Acid-catalyzed C-H Functionalization via Intermediate Peroxides (CHIPS)
06:34

Synthesis of Antiviral Tetrahydrocarbazole Derivatives by Photochemical and Acid-catalyzed C-H Functionalization via Intermediate Peroxides (CHIPS)

Published on: June 20, 2014

サイクロプロピルヒドロキシカルベン

David Ley1, Dennis Gerbig, J Philipp Wagner

  • 1Justus-Liebig University, Heinrich-Buff-Ring 58, 35392 Giessen, Germany.

Journal of the American Chemical Society
|July 29, 2011
PubMed
まとめ
この要約は機械生成です。

新型分子であるサイクロプロピルヒドロキシカルベンは,そのサイクロプロピル基により,半減期が著しく延長されています. この安定化は,そのπドナー能力と観測された[1,2]Hトンネリング行動に起因する.

さらに関連する動画

Accessing Valuable Ligand Supports for Transition Metals: A Modified, Intermediate Scale Preparation of 1,2,3,4,5-Pentamethylcyclopentadiene
09:45

Accessing Valuable Ligand Supports for Transition Metals: A Modified, Intermediate Scale Preparation of 1,2,3,4,5-Pentamethylcyclopentadiene

Published on: March 20, 2017

Isolating Free Carbenes, their Mixed Dimers and Organic Radicals
10:44

Isolating Free Carbenes, their Mixed Dimers and Organic Radicals

Published on: April 19, 2019

関連する実験動画

Last Updated: May 30, 2026

Synthesis of Antiviral Tetrahydrocarbazole Derivatives by Photochemical and Acid-catalyzed C-H Functionalization via Intermediate Peroxides (CHIPS)
06:34

Synthesis of Antiviral Tetrahydrocarbazole Derivatives by Photochemical and Acid-catalyzed C-H Functionalization via Intermediate Peroxides (CHIPS)

Published on: June 20, 2014

Accessing Valuable Ligand Supports for Transition Metals: A Modified, Intermediate Scale Preparation of 1,2,3,4,5-Pentamethylcyclopentadiene
09:45

Accessing Valuable Ligand Supports for Transition Metals: A Modified, Intermediate Scale Preparation of 1,2,3,4,5-Pentamethylcyclopentadiene

Published on: March 20, 2017

Isolating Free Carbenes, their Mixed Dimers and Organic Radicals
10:44

Isolating Free Carbenes, their Mixed Dimers and Organic Radicals

Published on: April 19, 2019

科学分野:

  • 物理化学 物理化学
  • 有機化学 オーガニック・ケミストリー
  • スペクトロスコーピーは,スペクトロスコーピーを用います.

背景:

  • カーベンは,有機合成において極めて重要な高度反応性の中間物質である.
  • ハイドロキシカルベンは,ユニークな電子特性を有するカルベンの特定のクラスです.
  • カーベンの安定性と反応性を理解することは,化学的変異を制御する上で鍵となる.

研究 の 目的:

  • サイクロプロピルヒドロキシカルベンを合成し,特徴づけるために.
  • サイクロプロピルヒドロキシカルベンの反応性と安定性,特にそのトンネリングの行動を調査する.
  • カーベンの性質を調節するサイクロプロピル置換剤の役割を明らかにする.

主な方法:

  • 960°Cでサイクルプロピルグリオキシル酸の高真空フラッシュ熱分解.
  • 11Kの固体アルゴンでマトリックス分離.
  • 特徴付けのための赤外線 (IR) スペクトロスコピー.
  • カルベンの反応を観察するための光分解研究.
  • 計算化学 (CCSD ((T) /cc-pVnZ//M06-2X/6-311++G ((d,p)) とトンネリング分析のためのウェンツェル・クレーマーズ・ブリルーイン形式主義.

主要な成果:

  • サイクロプロピルヒドロキシカルベンは成功裏に生成され,特徴づけられました.
  • 光分解により,カルベンは環の膨張を経て,新しい化合物であるサイクロブット-1-エン-1-オールに変化した.
  • マトリックスで分離されたサイクロプロピルヒドロキシカルベンは[1,2]Hトンネリングを示し,サイクロプロピルカルボックスアルデヒドを生成した.
  • サイクロプロピルグループは,親ヒドロキシメチレンと比較して,カルベンの半減期 (τ = 17.8 h at 11-20 K) を著しく増加させ,πドナー効果に起因した.
  • O-デュテラートアナログは,その構成でトンネリングがないことを確認しました.

結論:

  • サイクロプロピルヒドロキシカルベンは,半減期を大幅に延長した最初のヒドロキシカルベンです.
  • サイクロプロピル部分のπドナー能力は,ヒドロキシカルベンの安定化における支配的要因である.
  • 代替剤の電子ドナー能力は,ヒドロキシカルベンの半減期を決定する上で極めて重要です.