Oxidative cycloaddition of electron-deficient arenesulfonamides to hexa-1,5-diene

摘要

The reaction of electron-deficient arenesulfonamides 4-XC6H4SO2NH2 (X = Cl, NO2) with hexa-1,5-diene in the oxidative system t-BuOCl-NaI afforded cis- and trans-isomeric 1-(arenesulfonyl)-2,5-bis(iodomethyl)pyrrolidines. The diastereoisomers were separated, and their structure was determined by NMR spectroscopy and X-ray analysis. No further cyclization of these compounds into 3,8-diazabicyclo[3.2.1]-octanes was observed.