Friday, September 18, 2009
Reactions Using Iodine Azide without Explosions
How do you carry out organic synthesis when the reagent has a tendency to blow up? Brandt and Wirth constructed a microreactor to do the job. In this case, one of the main benefits of a microreactor is that very small amounts of material are needed. Once the reactants were mixed, they passed through a capillary with a volume of 0.196 mL where they were heated to promote the reaction.
The reaction of interest was between iodine azide and various derivatives of benzaldehyde. Under these conditions, the weak iodine - nitrogen bond breaks and the reaction involves a free radical mechanism. The aldehyde Hydrogen gets abstracted and the resulting radical reacts with iodine azide to give an acyl azide and more Iodine atoms to continue the radical chain reaction.
Brandt, J., & Wirth, T. (2009). Controlling hazardous chemicals in microreactors: Synthesis with iodine azide Beilstein Journal of Organic Chemistry, 5 DOI: 10.3762/bjoc.5.30