A Stereochemical Study of the Isomerization of Cyclopropyl Ethers to Allyl Ethers Catalyzed with Zinc Iodide.
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.
Sugimura
Takashi
T
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.
Futagawa
Tohru
T
Mori
Atsushi
A
Ryu
Ilhyong
I
Sonoda
Noboru
N
Tai
Akira
A