Related Experiment Video
Updated: Jan 22, 2026

Facile Preparation of 2Z,4E-Dienamides by the Olefination of Electron-deficient Alkenes with Allyl Acetate
Published on: June 21, 2017
Investigation of Transfer Group, Tether Proximity, and Alkene Substitution for Intramolecular Silyloxypyrone-Based [5
Jacob J Bulandr1, Jacob P Grabowski1, Chunyin M Law1
1Department of Chemistry , Illinois State University , Campus Box 4160, Normal , Illinois 61790-4160 , United States.
Abstract:
Systematic investigation of intramolecular silyloxypyrone-based [5 + 2] cycloadditions revealed three significant factors impacting conversion to cycloadduct: (1) the silyl transfer group has a substantial influence on the rate of reaction, and the robust t-butyldiphenylsilyl group was found to be more effective overall than the conventional t-butyldimethylsilyl group; (2) α,β-unsaturated esters were generally more reactive than terminal olefins and afforded appreciable quantity of cycloadduct even at room temperature; and (3) the proximity of the tether to the silyl transfer group revealed a critical alignment trend between the pyrone and the alkene. Taken together, these investigations provided insight regarding the steric and electronic parameters that impact the scope and limitation of these reactions.
More Related Videos
07:30A Direct, Regioselective and Atom-Economical Synthesis of 3-Aroyl-N-hydroxy-5-nitroindoles by Cycloaddition of 4-Nitronitrosobenzene with Alkynones
Published on: January 21, 2020
09:27A Magnetic Tether System to Investigate Visual and Olfactory Mediated Flight Control in Drosophila
Published on: November 21, 2008
Related Concept Videos
Intermolecular vs Intramolecular Forces
[4+2] Cycloaddition of Conjugated Dienes: Diels–Alder Reaction
Intramolecular Aldol Reaction
Cycloaddition Reactions: Overview
Radical Reactivity: Intramolecular vs Intermolecular
Nomenclature of Alkenes
As per the IUPAC rules, the longest carbon chain containing the maximum number of double bonds is identified as the parent chain and is numbered such that the doubly bonded carbon atoms receive the lowest possible numbers. The location of the double bond is indicated by the number of its first carbon atom. In branched...