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Related Concept Videos

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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Related Experiment Video

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

Cyclopropylhydroxycarbene.

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
Summary
This summary is machine-generated.

Cyclopropylhydroxycarbene, a novel molecule, exhibits a significantly prolonged half-life due to its cyclopropyl group. This stabilization is attributed to its π-donor capabilities and observed [1,2]H-tunneling behavior.

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

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Isolating Free Carbenes, their Mixed Dimers and Organic Radicals
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Isolating Free Carbenes, their Mixed Dimers and Organic Radicals

Published on: April 19, 2019

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

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

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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

Area of Science:

  • Physical Chemistry
  • Organic Chemistry
  • Spectroscopy

Background:

  • Carbenes are highly reactive intermediates crucial in organic synthesis.
  • Hydroxycarbenes are a specific class of carbenes with unique electronic properties.
  • Understanding carbene stability and reactivity is key to controlling chemical transformations.

Purpose of the Study:

  • To synthesize and characterize cyclopropylhydroxycarbene.
  • To investigate the reactivity and stability of cyclopropylhydroxycarbene, particularly its tunneling behavior.
  • To elucidate the role of the cyclopropyl substituent in modulating carbene properties.

Main Methods:

  • High-vacuum flash pyrolysis of cyclopropylglyoxylic acid at 960 °C.
  • Matrix isolation in solid Argon at 11 K.
  • Infrared (IR) spectroscopy for characterization.
  • Photolysis studies to observe carbene reactions.
  • Computational chemistry (CCSD(T)/cc-pVnZ//M06-2X/6-311++G(d,p)) and Wentzel-Kramers-Brillouin formalism for tunneling analysis.

Main Results:

  • Cyclopropylhydroxycarbene was successfully generated and characterized.
  • Upon photolysis, the carbene underwent ring expansion to cyclobut-1-en-1-ol, a novel compound.
  • Matrix-isolated cyclopropylhydroxycarbene exhibited [1,2]H-tunneling, yielding cyclopropylcarboxaldehyde.
  • The cyclopropyl group significantly increased the carbene's half-life (τ = 17.8 h at 11-20 K) compared to parent hydroxymethylene, attributed to π-donor effects.
  • O-deuterated analogue confirmed the absence of tunneling in that configuration.

Conclusions:

  • Cyclopropylhydroxycarbene is the first hydroxycarbene with a significantly prolonged half-life.
  • The cyclopropyl moiety's π-donor ability is a dominant factor in stabilizing hydroxycarbenes.
  • Electronic donor capabilities of substituents are critical in determining hydroxycarbene half-lives.