Abstract
In order to examine the effect of adjacent triple bond and phenyl group on the oxidation of methylene, oxidation of 1, 4-diphenyl-1-butyne with selenium dioxide was attempted. Further oxidation of its oxidation product with manganese dioxide and selective reduction of the unsaturated bond in both oxidation products, using palladium-barium sulfate as the catalyst were carried out. From infrared spectral measurement, it was suggested that the oxidized methylene group is not that adjacent to the phenyl ring but that adjacent to the triple bond and this was established through 2, 4-dinitrophenylhydrazone of an authentic sample synthesized by another route. The product formed by selenium dioxide oxidation was 1, 4-diphenyl-1-butyn-3-one and 1, 4-diphenyl-1-butyn-3-ol and not 1, 4-diphenyl-1-butyn-4-one or -4-ol.
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