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Related Concept Videos

Conformations of Cycloalkanes02:29

Conformations of Cycloalkanes

14.0K
Adolf von Baeyer attempted to explain the instabilities of small and large cycloalkane rings using the concept of angle strain — the strain caused by the deviation of bond angles from the ideal 109.5° tetrahedral value for sp3  hybridized carbons. However, while cyclopropane and cyclobutane are strained, as expected from their highly compressed bond angles, cyclopentane is more strained than predicted, and cyclohexane is virtually strain-free. Hence, Baeyer’s theory that...
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[3,3] Sigmatropic Rearrangement of 1,5-Dienes: Cope Rearrangement01:21

[3,3] Sigmatropic Rearrangement of 1,5-Dienes: Cope Rearrangement

3.3K
The Cope rearrangement is classified as a [3,3] sigmatropic shift in 1,5-dienes, leading to a more stable, isomeric 1,5-diene. The reaction involves a concerted movement of six electrons, four from two π bonds and two from a σ bond, via an energetically favorable chair-like transition state.
3.3K
[3,3] Sigmatropic Rearrangement of Allyl Vinyl Ethers: Claisen Rearrangement01:24

[3,3] Sigmatropic Rearrangement of Allyl Vinyl Ethers: Claisen Rearrangement

2.7K
The Claisen rearrangement is a [3,3] sigmatropic rearrangement of allyl vinyl ethers to unsaturated carbonyl compounds. The rearrangement is a concerted pericyclic reaction proceeding via a chair-like transition state.
2.7K
Thermal Electrocyclic Reactions: Stereochemistry01:17

Thermal Electrocyclic Reactions: Stereochemistry

2.5K
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.
2.5K
Cycloaddition Reactions: Overview01:16

Cycloaddition Reactions: Overview

3.3K
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.
3.3K
Cycloaddition Reactions: MO Requirements for Thermal Activation01:16

Cycloaddition Reactions: MO Requirements for Thermal Activation

4.2K
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.
4.2K

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Related Experiment Video

Updated: Jan 13, 2026

Efficient Construction of Drug-like Bispirocyclic Scaffolds Via Organocatalytic Cycloadditions of &#945;-Imino &#947;-Lactones and Alkylidene Pyrazolones
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Efficient Construction of Drug-like Bispirocyclic Scaffolds Via Organocatalytic Cycloadditions of α-Imino γ-Lactones and Alkylidene Pyrazolones

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Energy-Transfer-Enabled Skeletal Rearrangement of Cyclic Ketones into Strained Cyclopropane-Fused Medium Rings.

Yingru Xu1, Zehui Wang1, Jianjian Huang1

  • 1Hubei Key Laboratory of Bioinorganic Chemistry & Medica, Hubei Engineering Research Center for Biomaterials and Medical Protective Materials, School of Chemistry and Chemical Engineering, Huazhong University of Science and Technology (HUST), 1037 Luoyu Road, Wuhan, 430074, China.

Angewandte Chemie (International Ed. in English)
|January 10, 2026
PubMed
Summary
This summary is machine-generated.

Synthesizing cyclopropane-fused medium rings (CFMR) is now efficient using a novel photocatalytic skeletal editing strategy. This method transforms cyclic ketones into diverse CFMRs via a unique ring expansion-collapse cascade.

Keywords:
1,4‐Carbonyl migrationCyclic ketonesCyclopropane‐fused medium ringsPhotocatalysisRearrangement

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Solid-phase Synthesis of [4.4] Spirocyclic Oximes
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Solid-phase Synthesis of [4.4] Spirocyclic Oximes
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Solid-phase Synthesis of [4.4] Spirocyclic Oximes

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Area of Science:

  • Organic Chemistry
  • Photocatalysis
  • Synthetic Methodology

Background:

  • Cyclopropane-fused medium rings (CFMR) possess high strain and unique 3D structures.
  • Efficient and modular synthesis of CFMRs remains a significant challenge in organic chemistry.

Purpose of the Study:

  • To develop a general photocatalytic strategy for synthesizing diverse CFMRs.
  • To enable a direct topological leap in molecular structure from readily available precursors.

Main Methods:

  • A novel photocatalytic skeletal editing strategy was employed.
  • The transformation involves an energy-transfer-induced, diradical-mediated 1,4-carbonyl migration.
  • Density Functional Theory (DFT) calculations were used to support the proposed mechanism.

Main Results:

  • The strategy successfully synthesized diverse seven- to ten-membered CFMRs from five- to eight-membered cyclic ketones in a single step.
  • The transformation proceeds via a 'ring expansion-collapse' cascade, forming strained bicyclic frameworks.
  • Broad substrate scope, excellent functional-group compatibility, and high efficiency were demonstrated.

Conclusions:

  • The developed photocatalytic strategy offers a straightforward and efficient method for constructing CFMRs.
  • This approach allows for late-stage diversification of complex molecules and exploration of previously inaccessible CFMR chemical space.
  • Integration with further skeletal modifications enables rapid construction of versatile [n.3.0] bicycles.