title: A Stereochemical Study of the Isomerization of Cyclopropyl Ethers to Allyl Ethers Catalyzed with Zinc Iodide.
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.
authors.affiliation: Faculty 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.
authors.forename: Takashi
authors.initials: T
authors.lastname: Sugimura
authors.forename: Tohru
authors.initials: T
authors.lastname: Futagawa
authors.forename: Atsushi
authors.initials: A
authors.lastname: Mori
authors.forename: Ilhyong
authors.initials: I
authors.lastname: Ryu
authors.forename: Noboru
authors.initials: N
authors.lastname: Sonoda
authors.forename: Akira
authors.initials: A
authors.lastname: Tai