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

Abstract

The reaction of electron-deficient arenesulfonamides 4-XC 6 H 4 SO 2 NH 2 (X = Cl, NO 2 ) 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. n = 1, 2; EWG = COOEt, COMe, COPh, CN.