Journal of the Chemical Society. Perkin transactions II p. 1792 - 1799 (1980)
Update date:2022-08-03
Topics:
Ooi, Ngan Sim
Wilson, David A.
Salts of O-(benzimidoyl)benzamidoxime have been obtained by the action of N-chloro- or N-bromo-succinimide, or the halogens, on benzamidoxime.Acetylation of the free base gave the title compound, which underwent a thermal cyclisation, with loss of acetamide, to give 3,5-diphenyl-1,2,4-oxadiazole.The mechanism of the reaction, in diphenyl ether, closely paralleled the thermal cyclisation of O-acetylarylamidoximes and O-aroylacetamidoximes, and is thought to involve a polar cyclisation step followed by rate-determining proton transfer. 13C N.m.r. spectra for 32 oxime, amidoxime, O-acetylamidoxime, 5-methyl-1,2,4-oxadiazol-3-yl, and 3-methyl-1,2,4-oxadiazol-5-yl groups on the phenyl ring are calculated.
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