Abstract
An efficient and practical synthetic method for the preparation of five-membered ring compounds is reported. Carbocyclic and heterocyclic five-membered ring compounds bearing polyfluoroalkyl groups were obtained using Na 2S 2O4/NaHCO 3 promoted addition-cyclization of per(poly)fluoroalkyl iodides or perhaloalkanes with 1,6-heptadienes. The stereochemistry of hydrodehalogenation products ( 5, 6, 8, 9) was determined based on their 1H-NMR spectra. γ-Lactams and γ-lactones bearing fluoroalkyl groups were obtained using the same system promoted per(poly)fluoroalkylation reaction with N-allyl acrylamides ( 10) and allyl propiolate ( 15) under similar reaction conditions.
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