Cumene Hydroperoxide, CMHP

Cumene hydroperoxide is a relatively stable organic peroxide. This oxidizing agent is commercially available with a purity of ~80%. A 0.2 M solution in benzene has a half-life of 29 hours at 145°C. The decomposition products of cumene hydroperoxide are methylstyrene, acetophenone, and cumyl alcohol. Pure cumene hydroperoxide can be stored at room temperature, but the potential for an uncontrolled reaction and explosion is high. Cumyl as well as other hydroperoxides can undergo rapid decomposition under the influence of a wide range of trace compounds, such as acids and metals. (M. A. Francisco, Chem. Eng. News, 1993, 71, 4. Link).

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Recent Literature

A new catalytic system for the asymmetric epoxidation of allylic alcohols has been developed featuring high enantioselectivity for Z olefins, catalyst loading of less than 1 mol%, reaction temperatures of 0°C to room temperature over a shorter time, and simple workup procedures for small expoxy alcohols.
W. Zhang, A. Basak, Y. Kosugi, Y. Hoshino, H. Yamamoto, Angew. Chem. Int. Ed., 2005, 44, 4389-4391.

Chiral bishydroxamic acid ligands provided good yields and high enantioselectivities in the vanadium-catalyzed asymmetric epoxidation of homoallylic alcohols.
W. Zhang, H. Yamamoto, J. Am. Chem. Soc., 2007, 129, 286-287.

A new and efficient chiral catalyst system, lanthanum-chiral BINOL-tris(4-fluorophenyl)phosphine oxide-cumene hydroperoxide, was developed for the epoxidation of α,β-unsaturated ketones, thus providing the corresponding epoxy ketones with excellent enantioselectivities (up to >99% ee) in good to excellent yields at room temperature.
R. Kino, K. Daikai, T. Kawanami, H. Furuno, J. Inanaga, Org. Biomol. Chem., 2004, 2, 1822-1824.