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
Famous quotes containing the words reaction and/or mechanism:
“Christianity was only a very strong and singularly well-timed Salvation Army movement that happened to receive help from an unusual and highly dramatic incident. It was a Puritan reaction in an age when, no doubt, a Puritan reaction was much wanted; but like all sudden violent reactions, it soon wanted reacting against.”
—Samuel Butler (1835–1902)
“A mechanism of some kind stands between us and almost every act of our lives.”
—Sarah Patton Boyle, U.S. civil rights activist and author. The Desegregated Heart, part 3, ch. 2 (1962)