Halogenation of alkynes with Cl2 or Br2 can generally be

Chapter 10, Problem 10.73

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Halogenation of alkynes with Cl2 or Br2 can generally be achieved with high yields, while halogenation of alkynes with I2 typically gives low yields. However, the following reaction is successfully completed with I2 in high yields (94%) to afford a potentially useful functionalized and conformationally constrained diiododiene synthetic intermediate (Tetrahedron Lett. 1996, 37, 15711574). Propose a plausible mechanism for this transformation. I2 I I

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