Related Experiment Video
Updated: Apr 12, 2026

Microwave-assisted Intramolecular Dehydrogenative Diels-Alder Reactions for the Synthesis of Functionalized Naphthalenes/Solvatochromic Dyes
Published on: April 1, 2013
Nazarov reactions intercepted by (4 + 3) cycloadditions with oxygen-substituted dienes
François M LeFort1, Vinayak Mishra1, Graham D Dexter1
1Department of Chemistry, Dalhousie University, P.O. Box 15000, Halifax, Nova Scotia B3H 4R2, Canada.
Abstract:
The oxyallyl cation intermediate from the Lewis acid mediated Nazarov reaction of an allenyl vinyl ketone was intercepted by acyclic, 2-silyloxy-substituted butadienes by highly regioselective (4 + 3) cycloadditions. Stereoselectivity was often modest, but in some instances steric interactions were responsible for high selectivity. The results are consistent with concerted (4 + 3) cycloadditions. In many instances, the (4 + 3) products were susceptible to fragmentation or rearrangement in the presence of the Lewis acid.
Related Concept Videos
[4+2] Cycloaddition of Conjugated Dienes: Diels–Alder Reaction
Cycloaddition Reactions: Overview
Oxidation of Alkenes: Anti Dihydroxylation with Peroxy Acids
Cycloaddition Reactions: MO Requirements for Thermal Activation
Oxidation of Alkenes: Syn Dihydroxylation with Osmium Tetraoxide
Electrophilic 1,2- and 1,4-Addition of X2 to 1,3-Butadiene
![Cercosporin-Photocatalyzed [4+1]- and [4+2]-Annulations of Azoalkenes Under Mild Conditions](/_next/image?url=https%3A%2F%2Fcloudfront.jove.com%2FCDNSource%2Fteasers%2F60786.jpg&w=3840&q=50)
