CATALYTIC OXIDATION OF OLEFINS USING DIPHENYL DITELLURIDE
Reaction of aliphatic olefins with tert-butyl hydroperoxide and diaryl ditellurides in the presence of sulfuric acid in refluxing methanol gave methoxytellurenylation products with high regioselectivity having the aryltelluro group on the terminal carbon in the case of terminal olefins.The stereochemistry of the product from cyclohexene was trans.Under similar conditions, aromatic substituted olefins afforded vic-dimethoxyl compounds in the presence of catalytic amount of diaryl ditelluride.In this reaction, molecular oxygen (or air) as well as peroxidesand peracids were found to be effective as the oxidizing agent.The catalytic oxidation of olefins reported here proceeded in net syn fashion probably via anti methoxytellurenylation followed by displacement of the phenyltelluro group by a methoxy group with inversion.
NEW SYNTHETIC REACTIONS USING ARENETELLURINIC ANHYDRIDES
New synthetic reactions utilizing arenetellurinic acid anhydrides are described.The anhydrides proved to be very useful reagents for the transformation of various functional groups.Furthermore they induced various intramolecular cyclofunctionalizations to yield many oxygen and nitrogen heterocycles.
Hu, Nan Xing,Aso, Yoshio,Otsubo, Tetsuo,Ogura, Fumio
p. 177 - 190
(2007/10/02)
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