1247181-41-4Relevant academic research and scientific papers
Alkene dihydroxylation with malonoyl peroxides: Catalysis using fluorinated alcohols
Picon, Sylvain,Rawling, Michael,Campbell, Matthew,Tomkinson, Nicholas C. O.
, p. 6250 - 6253 (2013/02/23)
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.
Alkene syn dihydroxylation with malonoyl peroxides
Griffith, James C.,Jones, Kevin M.,Picon, Sylvain,Rawling, Michael J.,Kariuki, Benson M.,Campbell, Matthew,Tomkinson, Nicholas C. O.
supporting information; experimental part, p. 14409 - 14411 (2010/12/24)
Cyclopropyl malonoyl peroxide (1), which can be prepared in a single step from the commercially available diacid, is an effective reagent for the dihydroxylation of alkenes. Reaction of 1 with an alkene in the presence of 1 equiv of water at 40 °C followed by alkaline hydrolysis leads to the corresponding diol (40-93%). With 1,2-disubstituted alkenes, the reaction proceeds with syn selectivity (3:1 to >50:1). A mechanism consistent with the experimental findings that is supported by oxygen-labeling studies is proposed.
