Muhammad Javed - Synthetic Approaches to Bicyclic Diazenium Salts

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      An alternative route for the synthesis of diazenium salts by the   reaction of hydrazones with dimethylsulfonium ditriflate is   described.


      Bicyclic diazenium salts have been prepared from α-chloroazo   species via a Lewis acid-mediated intramolecular cycloaddition.   An alternative, more direct, route to these salts by the reaction   of hydrazones with dimethylsulfonium ditriflate is also   described. Terminal olefins provided mixtures of fused and   bridged bicyclic diazenium salts. The ratio of the fused and   bridged species was observed to depend on the electronics of the   N-aryl substituent, which is explained by considering a concerted   asynchronous cycloaddition mechanism.

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