A stereochemical study of the isomerization of cyclopropyl ethers to allyl ethers catalyzed with zinc iodide

Takashi Sugimura*, Tohru Futagawa, Atsushi Mori, Ilhyong Ryu, Noboru Sonoda, Akira Tai

*Corresponding author for this work

Research output: Contribution to journalArticlepeer-review

20 Scopus citations

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.

Original languageEnglish
Pages (from-to)6100-6103
Number of pages4
JournalJournal of Organic Chemistry
Volume61
Issue number18
DOIs
StatePublished - 6 Sep 1996

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