Synthesis of Alkyl Azides with a Polymeric Reagent

Many desirable features of an alkyl azide synthesis—among other things reaction at rom temperature in organic solvents, work-up without introduction of heat—are combined in the use of the novel “azidizing” polymer 1. The polymer 1 was prepared from Amberlite IR-400 and NaN3, allowed to react in ca. tenfold excess with alkyl halides or tosylates (almost always quantitative) and simply filtered from the solutions of the alkyl azides. Even the synthesis of CH2(N3)2 from CH2Cl2 could be achieved with this method.