Iodination of alkenes to give vicinal diiodides (1,2-diiodides)

by James

Description: Treatment of alkenes with iodine (I2) leads to the formation of vicinal diiodides (1,2-diiodides).

Notes: The iodides add to opposite faces of the double bond (“anti addition”)

Examples: 


Notes: Note that the stereochemistry is trans in these products.

Mechanism: Attack of the alkene on iodine gives the iodonium ion (Step 1, arrows A and B). The iodonium ion is then attacked by iodide ion at the most substituted carbon where applicable (Markovnikoff) to give the 1,2-diiodide.


 

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