title: Alkene dihydroxylation with malonoyl peroxides: catalysis using fluorinated alcohols.
abstract: The effect of fluorinated alcohols on the dihydroxylation of alkenes using cyclopropyl malonoyl peroxide is described. Addition of perfluoro-tert-butyl alcohol to a toluene solution of alkene and peroxide increases the rate of product formation and the stereoselectivity observed, providing a simple and effective method for acceleration of this important class of reaction. Basic hydrolysis of the crude reaction mixture provides access to syn-diols in high yield and stereoselectivity.
authors.affiliation: School of Chemistry, Main Building, Cardiff University, Park Place, Cardiff, CF10 3AT, UK.
authors.forename: Sylvain
authors.initials: S
authors.lastname: Picon
authors.forename: Michael
authors.initials: M
authors.lastname: Rawling
authors.forename: Matthew
authors.initials: M
authors.lastname: Campbell
authors.forename: Nicholas C O
authors.initials: NC
authors.lastname: Tomkinson
mesh_terms: D000438:Alcohols / Q000138:chemical synthesis* / Q000737:chemistry; D000475:Alkenes / Q000737:chemistry*; D002384:Catalysis; D006845:Hydrocarbons, Fluorinated / Q000737:chemistry*; D006868:Hydrolysis; D006900:Hydroxylation; D015394:Molecular Structure; D010545:Peroxides / Q000737:chemistry*
chemical_list: D000438:Alcohols; D000475:Alkenes; D006845:Hydrocarbons, Fluorinated; D010545:Peroxides