Photoreaction of N,N'-Dibromo-2,5-piperazinedione

Article abstract of DOI:10.1246/bcsj.54.3453

The photolysis of N,N'-dibromo-2,5-piperazinedione in dichloromethane gave an unstable photoproduct.The alcoholysis of the photoproduct in the presence of a small amount of hydrogen bromide yielded 3,6-diethoxy-2,5-piperazinedione and its alcoholyzed products, ethyl diethoxyacetate, ethyl 2-(diethoxyacetylamino)-2-ethoxyacetate, N-(1-ethoxy-1-ethoxycarbonylmethyl)oxamide, and ethyl N-(diethoxyacetyl)glycinate.The reactions of the photoproduct with other nucleophiles also gave the corresponding substituted 2,5-piperazinediones.The structure of the primary photoproduct was deduced to be 3,6-dibromo-2,5-piperazinedione on the basis of these observations.