RUTHENIUM-CATALYZED EPOXIDATION OF UNFUNCTIONALIZED OLEFINS WITH TERT-BUTYL HYDROPEROXIDE

Authors
BARF GA VANDENHOEK D SHELDON RA
Citation
Ga. Barf et al., RUTHENIUM-CATALYZED EPOXIDATION OF UNFUNCTIONALIZED OLEFINS WITH TERT-BUTYL HYDROPEROXIDE, Tetrahedron, 52(40), 1996, pp. 12971-12978
Citations number
47
Categorie Soggetti
Chemistry Inorganic & Nuclear
Journal title
Tetrahedron → ACNP
ISSN journal
00404020
Volume
52
Issue
40
Year of publication
1996
Pages
12971 - 12978
Database
ISI
SICI code
0040-4020(1996)52:40<12971:REOUOW>2.0.ZU;2-8
Abstract
A number of unfunctionalized aromatic and aliphatic olefins was tested in ruthenium-catalyzed epoxidation with tert-butyl hydroperoxide as t he external oxidant. The effect of reaction without ligands and with t wo different type of ligands was investigated. Olefins containing term inal double bonds afforded low epoxide selectivities, whereas secondar y and tertiary olefins afforded up to 80% selectivity for the epoxide. A mechanism for the ruthenium-catalyzed epoxidation with tert-butyl h ydroperoxide is proposed. Copyright (C) 1996 Elsevier Science Ltd