Shioiri-Ninomiya-Yamada modification

Because the Shioiri modification avoids isolation of the intermediate acyl azide, it is particularly well suited for cases in which the azide intermediate would be particularly unstable. The case of 1,3,5-benzenetricarbonyl azide (45) was mentioned earlier. Another instance is the diacyl azide derived from 1,4-cubane dicarboxylic acid An early attempt to prepare diaminocubane via Curtius rearrangement of the diacyl azide was abandoned when the first sample of the crystalline eizide exploded violently. However, the Shioiri-Ninomiya-Yamada conditions smoothly... 

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