The synthesis of 1,2,4-oxadiazoles under high pressure.
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The reactions of benzamidoxime with benzonitrile or acetonitrile did not occur under ordinary pressure, but they proceeded smoothly under several handred MPa pressure to give 3, 5-diphenyl- or 3-phenyl-5-methyl-1, 2, 4-oxadiazoles, [1a, b], respectively. The pressure effect on these reactions were surveyed and their activation volumes (ΔV<SUP>≠</SUP>) were estimated to be -14.6 and 18.5 ml.mol<SUP>-1</SUP>, respectively. Upon treatment with disubstituted cyanamides, amidoximes gave 5-amino-1, 2, 4-oxadiazoles, [3] together with a small amount of the corresponding 5-diaminomethyleneamino compounds, [4], while [4] were obtained as main products when the above reactions were carried out under 400 MPa pressure. It was thus found that the reactions of amidoximes with nitriles and disubstituted cyanamides are significantly promoted under pressure to afford a number of novel 1, 2, 4oxadiazole compounds.
- 公益社団法人 日本化学会の論文
公益社団法人 日本化学会 | 論文
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