Science of Synthesis

Parrain, J.-L.; Thibonnet, J., Science of Synthesis, (2005) 26, 767.

Like the preparation of dichloro or dibromo ketones, α,α-diiodo ketones can be prepared by direct iodination of ketones. Iodine in the presence of a base has mainly been used in these reactions and generally α,α-diiodo ketones are obtained in fair to good yields. For example, reaction of the methoxyestrone ‌55‌ with iodine in the presence of potassium hydroxide in methanol affords the α,α-diiodo(methoxy)estrone ‌56‌ in 85% yield (‌Scheme 28‌).[‌135‌,‌136‌] Dibenzoylmethane undergoes similar iodination using an excess of iodine–hydriodic acid in acetic acid to give dibenzoyldiiodomethane.[‌137‌] A process for the transformation of 11β,17α-dihydroxy-6α-methylpregna-1,4-diene-3,20-dione 17-acetate into 11β,17α,21-trihydroxy-6α-methylpregna-1,4-diene-3,20-dione 21-acetate has been described via a diiodo ketone intermediate.[‌138‌]

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References

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• 8.Meeeee-Meee, (8888) 8/8, 888.