MILD SYNTHESIS OF AZIDES BY MEANS OF A POLYMERIC REAGENT.

Organic azides are useful intermediates in the synthesis of pharmaceuticals, pesticides and photoaffinity labels. However, most methods leading to alkyl azides require either heating during their synthesis or purification by distillation, which is undesirable because of the thermal instability of these compounds. We have discovered a method that permits clean conversion of alkyl halides or sulfonates into alkyl azides by means of a polymeric reagent. The reaction proceeds under mild conditions at room temperature in a variety of solvents. The reaction can be monitored by GC or TLC. The polymer is removed by filtration and can be easily regenerated, and azide products are obtained cleanly without heating. Specific examples are discussed.