993-71-5Relevant academic research and scientific papers
A Highly Efficient Osmium Tetraoxide Catalyzed Oxidation of Sterically Hindered Olefins to Diols
Ray, Rahul,Matteson, Donald S.
, p. 119 - 123 (2007/10/02)
The use of trimethylamine oxide as oxidizing agent in the presence of catalytic amounts of osmium tetraoxide and pyridine in refluxing aqueous t-butyl alcohol efficiently converts sterically hindered olefins to diols without forming the α-hydroxy ketones or other by-products encountered with previously known procedures.Trisubstituted olefins with which this procedure has proved successful include α-pinene, the methyl and methoxyethoxymethyl ethers of nopol, ethyl chrysanthemumate, and, marginally, 3-methyl-3-penten-2-one.The disubstituted olefins cyclooctene and E-4-methyl-2-pentene were hydroxylated efficiently.The new procedure also proved more efficient than t-butyl hydroperoxide for hydroxylation of tetramethylethylene.Pyridine not only failed to enhance but substantially reduced the relatively mediocre yield of diol from α-pinene when N-methylmorpholine N-oxide was used as oxidizing agent.
