N-Chloro Nylons as Polymer Reagents

A series of N-chlorinated nylons were prepared so that in most cases more than 90% of the N—H bonds were converted to N—Cl bonds. Suitable chlorinating reagents were t-butyl hypochlorite, chlorine monoxide in carbon tetrachloride, and aqueous hypochlorous acid. Chemical and spectroscopic evidence helped confirm the N—Cl polymeric structures. The N-chlorinated polymers were found to readily oxidize secondary and primary alcohols in the same manner as low molecular weight N-halogenated amides and imides. The N-chlorinated polymers were also found suitable for the oxidation of sulfides to sulfoxides. In most cases of the oxidation of alcohols and sulfides, the polymers formed an insoluble powder which was readily removed by filtration, facilitating the work-up of the desired product.