Cerium(IV) Trifluoroacetate


[52118-96-4]  · C8CeF12O8  · Cerium(IV) Trifluoroacetate  · (MW 592.17)

(oxidizing agent for aromatic hydrocarbons)

Solubility: sol acetone, DME, DMSO, acetonitrile, TFA containing lithium trifluoroacetate; insol chloroform, dichloromethane, benzene.

Form Supplied in: yellow solid.

Preparative Methods: by the reaction of cerium(IV) hydroxide with TFA to give the basic salt Ce(OH)2(O2CCF3)2, which on further treatment with TFA and its anhydride affords the desired reagent.1 Thus far the reagent has only been used in the crude state without purification.

Handling, Storage, and Precautions: is sensitive to moisture and light and should therefore be stored under nitrogen and protected from light.

Oxidations of Arenes.

Cerium(IV) trifluoroacetate reacts instantaneously at room temperature with methylbenzenes to give coupling products.1 For example, durene is oxidized rapidly in TFA containing cerium trifluoroacetate to give a diphenylmethane derivative (eq 1).

Reaction of anthracene with cerium(IV) trifluoroacetate in alcohols provides 9-alkoxyanthracenes (eq 2).2 Use of lower alcohols affords the corresponding 9-alkoxyanthracenes in good yields, while reaction of higher alcohols results in poor yields of the products, a significant amount of anthraquinone being formed.

1. Norman, R. O. C.; Thomas, C. B.; Ward, P. J. JCS(P1) 1973, 2914.
2. Sugiyama, T. CL 1987, 1013.

Tsuneo Imamoto

Chiba University, Japan

Copyright 1995-2000 by John Wiley & Sons, Ltd. All rights reserved.