References

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Mechanism for the oxidation of alcohols by IBX

Satam, V.; Harad, A.; Rajule, R.; Pati, H. Tetrahedron 2010, 66, 7659-7706.

This paper proposed a mechanism for the oxidation of an alcohol to a ketone using 2-iodoxybenzoic acid (IBX). IBX is converted to iodosobenzoic acid (IBA) in the process. In the fast step of the reaction, the hydroxyl group of IBX is protonated. The alcohol oxygen atom’s lone pairs attack the iodine atom, forming a new I-O bond, and a molecule of water is released. The alcohol oxygen is then deprotonated. In the second slower step, the pi bond between the iodine and oxygen atom attacks a hydrogen atom bonded to a carbon atom attached to the oxygen atom of the original alcohol. A double bond is formed between this carbon and oxygen atom, producing the desired ketone. The bond between the iodine atom and ketone oxygen is broken. The negatively charged oxygen atom still attached to the iodine atom is protonated, resulting in iodosobenzoic acid.

This paper has been cited by:

1. Cui, L.; Zhi-Lei, D.; Kai, L. Org. Lett. 2011,13, 6488-6491. This paper describes the use of an IBX derivative to oxidize a keto ester to its corresponding dehydrogenated product.
2. Moorthy, J.N.; Senapati, K.; Parida, K.N. J. Org. Chem. 2011, 76, 9593-9601. This paper studies the oxidation of various alcohols and sulfides using TetMe-IBX, whose methyl groups lower the activation energy.
3. Bartlett, S.L.; Beaudry, C.M. J. Org. Chem. 2011, 76, 9852-9855. This paper demonstrates the oxidation of hydroxyketones to diketones using IBX.