A convenient method for the addition of HI to unsaturated hydrocarbons using I2 on Al2O3

✍ Scribed by Lyman J. Stewart; Gray Donna; Pagni M. Richard; Kabalka W. George

• Publisher: Elsevier Science
• Year: 1987
• Tongue: French
• Weight: 109 KB
• Volume: 28
• Category: Article
• ISSN: 0040-4039
• DOI: 10.1016/s0040-4039(00)96546-8

✦ Synopsis

Iodine reacts, under mild conditions, with hydroxyl groups on the surface of alumina to form HI which readily adds to unsaturated hydrocarbons to form alkyl and vinyl iodides.

In 1986 we reported that aromatic substrates react with 12 on dehydrated alumina to give iodinated aromatic products. I Toluene, for example, gave a mixture of g-, ;-, and p-iodotoluene.

Although the electrophile was not identified, it was most likely either I2 polarized by partially exposed Al +3 or 01-formed in the reaction of surface O-2 or OH-with 12. We now report that I2 on dehydrated alumina also reacts with surface hydroxyl groups to form HI which readily adds to many unsaturated hydrocarbons.