Related Experiment Video
Updated: Jan 13, 2026

The Preparation and Properties of Thermo-reversibly Cross-linked Rubber Via Diels-Alder Chemistry
Published on: August 25, 2016
Thermally Induced Intramolecular Diels-Alder Reaction of Furan-Tethered Methylenecyclopropanes
Qi-Yun Huang1, Xin-Tao Gu2, Yin Wei2
1Key Laboratory for Advanced Materials, Institute of Fine Chemicals, School of Chemistry & Molecular Engineering, East China University of Science and Technology, 130 Meilong Road, Shanghai 200237, China.
Abstract:
The substantial ring strain and activated double bonds render methylenecyclopropanes (MCPs) potential substrates for Diels-Alder (DA) reactions. In this work, we present a thermally induced intramolecular Diels-Alder (IMDA) reaction utilizing furan-tethered MCPs. The reactions were carried out smoothly with respect to a wide variety of substrates with good functional group compatibility, affording the desired products in moderate to excellent yields. The synthetic utility of these products was successfully demonstrated. Mechanistic studies involving radical scavenger control experiments and density functional theory (DFT) calculations revealed a concerted mechanism involving an asynchronous one-step pathway.
More Related Videos
12:07Microwave-assisted Intramolecular Dehydrogenative Diels-Alder Reactions for the Synthesis of Functionalized Naphthalenes/Solvatochromic Dyes
Published on: April 1, 2013
10:10Application of Elemental Lanthanides in the Selective C-F Activation of Trifluoromethylated Benzofulvenes Providing Access to Various Difluoroalkenes
Published on: July 28, 2018
Related Concept Videos
[4+2] Cycloaddition of Conjugated Dienes: Diels–Alder Reaction
Diels–Alder Reaction Forming Cyclic Products: Stereochemistry
Diels–Alder Reaction Forming Bridged Bicyclic Products: Stereochemistry
Diels–Alder Reaction: Characteristics of Dienes
Characteristics of the diene
Conformation
The simplest example of a diene is 1,3-butadiene, an acyclic conjugated π system. At room temperature, the molecule exists as a mixture of s-cis and s-trans conformers by virtue of rotation around the carbon–carbon single bond. Although the s-trans isomer is more stable,...
Diels–Alder vs Retro-Diels–Alder Reaction: Thermodynamic Factors
Diels–Alder Reaction: Characteristics of Dienophiles
Characteristics of Dienophiles
Generally, the best dienophiles are alkenes containing electron-withdrawing substituents such as carbonyl, nitrile, and nitro groups. The feasibility of a Diels–Alder reaction depends...