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Related Concept Videos

Cyclohexenones via Michael Addition and Aldol Condensation: The Robinson Annulation01:27

Cyclohexenones via Michael Addition and Aldol Condensation: The Robinson Annulation

Robinson annulation is a base-catalyzed reaction for the synthesis of 2-cyclohexenone derivatives from 1,3-dicarbonyl donors (such as cyclic diketones, β-ketoesters, or β-diketones) and α,β-unsaturated carbonyl acceptors. Named after Sir Robert Robinson, who discovered it, this reaction yields a six-membered ring with three new C–C bonds (two σ bonds and one π bond).
Halogenation of Alkenes02:46

Halogenation of Alkenes

Halogenation is the addition of chlorine or bromine across the double bond in an alkene to yield a vicinal dihalide. The reaction occurs in the presence of inert and non-nucleophilic solvents, such as methylene chloride, chloroform, or carbon tetrachloride.
Consider the bromination of cyclopentene. Molecular bromine is polarized in the proximity of the π electrons of cyclopentene. An electrophilic bromine atom adds across the double bond, forming a cyclic bromonium ion intermediate.
Formation of Halohydrin from Alkenes02:41

Formation of Halohydrin from Alkenes

An alkene, such as propene, reacts with bromine in the presence of water to yield a halohydrin. Halohydrins contain a halogen and a hydroxyl group attached to adjacent carbons. When the halogen is bromine, it is called a bromohydrin, while a chlorohydrin has chlorine as the halogen.
Cycloaddition Reactions: Overview01:16

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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.
Stability of Substituted Cyclohexanes02:30

Stability of Substituted Cyclohexanes

This lesson discusses the stability of substituted cyclohexanes with a focus on energies of various conformers and the effect of 1,3-diaxial interactions.
The two chair conformations of cyclohexanes undergo rapid interconversion at room temperature. Both forms have identical energies and stabilities, each comprising equal amounts of the equilibrium mixture. Replacing a hydrogen atom with a functional group makes the two conformations energetically non-equivalent.
For example, in...
Cycloaddition Reactions: MO Requirements for Thermal Activation01:16

Cycloaddition Reactions: MO Requirements for Thermal Activation

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.

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Preparation of a Corannulene-functionalized Hexahelicene by Copper(I)-catalyzed Alkyne-azide Cycloaddition of Nonplanar Polyaromatic Units
09:35

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Cyclohexanones by Rh-mediated intramolecular C-H insertion.

Douglass F Taber1, Craig M Paquette, Peiming Gu

  • 1Department of Chemistry and Biochemistry, University of Delaware , Newark, Delaware 19716, United States.

The Journal of Organic Chemistry
|August 31, 2013
PubMed
Summary
This summary is machine-generated.

Rh catalysis enables efficient cyclization of long chain α-aryl α-diazo ketones into cyclohexanones. This outcome differs significantly from related α-diazo β-ketoesters, which yield cyclopentanones.

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Area of Science:

  • Organic Chemistry
  • Catalysis
  • Synthetic Methodology

Background:

  • Diazo compounds are versatile synthetic intermediates in organic chemistry.
  • Rhodium (Rh) catalysis is widely employed for various organic transformations.
  • Cyclization reactions are crucial for constructing cyclic organic molecules.

Purpose of the Study:

  • To investigate the cyclization of long chain α-aryl α-diazo ketones using Rh catalysis.
  • To compare the reaction outcomes with those of α-diazo β-ketoesters.
  • To explore the formation of cyclohexanone products from α-diazo ketones.

Main Methods:

  • Employing Rhodium (Rh) catalysis.
  • Utilizing long chain α-aryl α-diazo ketones as substrates.
  • Analyzing reaction products for structural identification.

Main Results:

  • Efficient cyclization of α-aryl α-diazo ketones to cyclohexanones was achieved.
  • A marked contrast was observed compared to the cyclization of α-diazo β-ketoesters.
  • Cyclization of α-diazo β-ketoesters consistently yielded cyclopentanone products.

Conclusions:

  • Long chain α-aryl α-diazo ketones undergo Rh-catalyzed cyclization to form cyclohexanones.
  • The reaction pathway for α-aryl α-diazo ketones differs from that of α-diazo β-ketoesters.
  • This study highlights a novel synthetic route to cyclohexanones.