Fe(ii)-Catalyzed azidation of polybutadienes using the Zhdankin reagent

Abstract

Phenyl-terminated polybutadienes (PtPBs) are efficiently converted to azidated PtPBs using the Zhdankin reagent generated in situ from commercially available iodosobenzoic acid and TMSN₃ with an iron catalyst. A key strategy for the direct introduction of azide groups into the double bonds in polybutadiene is by using the Zhdankin reagent acting as a stable cyclic azidoiodinane. These reactions are very mild and the azidation rates can be easily controlled by adjusting the amount of reagents. PtPBs containing various azide contents (5%, 10%, and 15%) could be obtained. The properties of these azidated polybutadienes were determined and their spectral data were collected.