DERIVATIVES OF SUBSTITUTED SUCCINIC ACIDS: I. THE ACTION OF ALKALINE SODIUM HYPOBROMITE ON 1,2-DIPHENYLSUCCINAMIDE AND 3,4-DIPHENYLSUCCINIMIDE
- 1 November 1934
- journal article
- Published by Canadian Science Publishing in Canadian Journal of Research
- Vol. 11 (5) , 628-636
- https://doi.org/10.1139/cjr34-120
Abstract
The application of the Hofmann reaction for the preparation of amines from amides to 1:2-diphenylsuccinamide has led to none of the expected substances, but to diphenylacetic acid as the principal product of the reaction. The isolation of this substance indicates that at some stage a rearrangement has occurred. The mechanism of the rearrangement is obscure but oxidation to a 1,2-dihydroxydiamide may be the first stage. This is supported by the conversion of diphenylsuccinimide into diphenylmaleic anhydride by alkaline sodium hypobromite.Various derivatives of diphenylsuccinic acid, which were obtained in unsuccessful attempts to prepare in quantity other 1:2-diarylsuccinamides, are described.Keywords
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