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Updated: Oct 3, 2026

Facile Preparation of (2Z,4E)-Dienamides by the Olefination of Electron-deficient Alkenes with Allyl Acetate
Published on: June 21, 2017
A Stereochemical Study of the Isomerization of Cyclopropyl Ethers to Allyl Ethers Catalyzed with Zinc Iodide
Takashi Sugimura1, Tohru Futagawa, Atsushi Mori
1Faculty of Science, Himeji Institute of Technology, Kanaji, Kamigori, Ako-gun 678-12, Japan, and Department of Applied Chemistry, Faculty of Engineering, Osaka University, Suita, Osaka 565 Japan.
Abstract:
Optically active 1-alkoxybicyclo[4.1.0]heptane was converted using zinc iodide as a catalyst to 2-alkoxymethylidenecyclohexane without loss of optical purity. The mechanism of the isomerization was studied using a stereochemical analysis of the product and deuterium labeling experiments. The results indicated that the isomerization takes place through a stepwise mechanism that involves an attack of zinc iodide on the cyclopropane ring to cause ring opening, followed by an intramolecular 1,2-hydride shift with liberation of the zinc iodide.
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