The Journal of Organic Chemistry

Electrooxidative cyclization of N-acylhydrazones of aldehydes and ketones to. DELTA. 3-1, 3, 4-oxadiazolines and 1, 3, 4-oxadiazoles

T Chiba, M Okimoto

Index: Chiba, Toshiro; Okimoto, Mitsuhiro Journal of Organic Chemistry, 1992 , vol. 57, # 5 p. 1375 - 1379

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Citation Number: 81

Abstract

The electrolytic oxidation of ketone N-acylhydrazones (1) in methanolic sodium acetate induced their intramolecular cyclization to the corresponding 2-methoxy-A3-l, 3, 4- oxadiazolines 3. The thermal stability of a given oxadiazoline and what products were formed by its thermal decomposition was found to depend on the natures of the substituents at C-2. Thus, 2-methoxy-2-phenyloxadiazolines preferentially yielded osiranes 5, whereas ...

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