Reaction of enol ethers with zinc carbenoid reagents. Cyclopropanation and subsequent isomerization to allylic ethers

Ilhyong Ryu*, Tomoyuki Aya, Shoji Otani, Shinji Murai, Noboru Sonoda

*Corresponding author for this work

Research output: Contribution to journalArticlepeer-review

20 Scopus citations

Abstract

The reactions of enol ethers (ROCC, R = alkyl, silyl) with zinc carbenoid reagents were found to give allylic ethers in several cases along with the expected cyclopropyl ethers. The ratio of these two products was highly dependent on the concentration of the reaction mixture. Thus, the selective formation of each product was conveniently attained by merely changing the amounts of the solvent used. Zinc iodide, a by-product of the reaction, plays a key role in the present cyclopropyl to allylic rearrangement. Ring-opened ionic intermediates are proposed.

Original languageEnglish
Pages (from-to)279-290
Number of pages12
JournalJournal of Organometallic Chemistry
Volume321
Issue number3
DOIs
StatePublished - 10 Apr 1987

Fingerprint Dive into the research topics of 'Reaction of enol ethers with zinc carbenoid reagents. Cyclopropanation and subsequent isomerization to allylic ethers'. Together they form a unique fingerprint.

Cite this