Reaction Mechanism
The reaction mechanism proposed in the original Barton publication is outlined as follows:
The hydrazone is oxidized by iodine into a diazo intermediate. In the next step, iodine reacts as a nucleophile; displacement of nitrogen then generates an iodocarbonium ion. When the reaction site is not sterically hindered, a second iodide can recombine to form the geminal di-iodide; otherwise an elimination reaction leads to the vinyliodide. When water is present, the reaction product can revert to the ketone.
This reaction is related to the Shapiro reaction.
Read more about this topic: Hydrazone Iodination
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