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
Synthesis of Fused and Bridged Bicyclic Diazenium Salts by Intramolecular Cycloaddition
作者:Muhammad I. Javed、Jodi M. Wyman、Matthias Brewer
DOI:10.1021/ol900502s
日期:2009.5.21
Bicyclic diazenium salts were efficiently prepared by a Lewis acid mediated intramolecularcycloaddition. Terminal olefins provided mixtures of fused and bridged bicyclic diazenium salts. The α-chloroazo cycloaddition precursors were conveniently prepared from the corresponding phenyl hydrazones by treatment with chlorodimethylsulfonium chloride.