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Updated: May 13, 2026

Facile Preparation of (2Z,4E)-Dienamides by the Olefination of Electron-deficient Alkenes with Allyl Acetate
Published on: June 21, 2017
Subtle electronic effects in metal-free rearrangement of allenic alcohols
Venkata R Sabbasani1, Phani Mamidipalli, Huijie Lu
1Department of Chemistry, University of Illinois at Chicago, 845 West Taylor Street, Chicago, Illinois 60607, United States.
Abstract:
A general and stereoselective rearrangement of allenic alcohols to (E,E)-1,3-dien-2-yl triflates and chlorides was developed under metal-free conditions. Subtle electronic effects of the alkyl and aryl substituents on the carbon bearing the hydroxyl group has a profound impact on the reaction rate and efficiency such that vinyl triflates were obtained from electron-deficient substrates and trimethylsilyl triflate whereas vinyl chlorides were generated with an electron-rich substrate and trimethylsilyl chloride.
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