Skeletal reorganization of enynes into 1-vinylcycloalkenes in ionic liquids

Yuhei Miyanohana; Hiroki Inoue; Naoto Chatani

doi:10.1021/jo0489061

Skeletal reorganization of enynes into 1-vinylcycloalkenes in ionic liquids

J Org Chem. 2004 Nov 26;69(24):8541-3. doi: 10.1021/jo0489061.

Authors

Yuhei Miyanohana¹, Hiroki Inoue, Naoto Chatani

Affiliation

¹ Department of Applied Chemistry, Faculty of Engineering, Osaka University, Suita, Osaka 565-0871, Japan.

PMID: 15549840
DOI: 10.1021/jo0489061

Abstract

The skeletal reorganization of enynes catalyzed by transition metal chlorides, such as PtCl(2), [RuCl(2)(CO)(3)](2), [RhCl(CO)(2)](2), and AuCl(3), in ionic liquids proceeds under milder conditions (at lower reaction temperatures and for shorter reaction times) than those needed for ordinary solvents. The products produced by the skeletal reorganization of enynes were easily removed from the catalyst by a simple extraction with Et(2)O or distillation. The PtCl(2) can be reused up to five times.