ISOMERIC SYDNONES: I. THE REACTIONS OF 1- AND 2-BENZOYL-1-METHYLHYDRAZINES AND PHOSGENE
- 1 May 1965
- journal article
- Published by Canadian Science Publishing in Canadian Journal of Chemistry
- Vol. 43 (5) , 1607-1613
- https://doi.org/10.1139/v65-212
Abstract
The oxygen–carbonyl isomeric sydnone (V) has been synthesized from 1-benzoyl-1-methyl-hydrazine hydrochloride (VII) and phosgene. The isosydnone V itself reacts with phosgene to form 2-chloro-5-phenyl-1,3,4-oxadiazole (VI), a new substituted 1,3,4-oxadiazole. Thermal rearrangement of the salt VII takes place at 200° to give 1-benzoyl-2-methylhydrazine, which with phosgene forms the isomer XI. Some mechanistic pathways for these transformations are discussed.Keywords
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