Alkyl aryl ketones are converted into the corresponding α-sulfonyloxyketones, in moderate
to excellent yields, via a novel procedure that utilizes Oxone®, p-toluenesulfonic acid or methanesulfonic acid and molecular iodine in a mixture of
acetonitrile and 2,2,2-trifluoroethanol. The yield is found to be dependent on the
nature of the ketone. A mechanism is proposed in which the key intermediates are an
α-iodoketone and a subsequently formed α-iodosylketone. The latter reacts with the
sulfonic acid to afford the α-sulfonyloxyketone product.
Key words
α-sulfonyloxyketones - Oxone
®
- molecular iodine -
p-toluenesulfonic acid - methanesulfonic acid
