Organic Chemistry Portal
Chemicals >> Oxidizing Agents


Examples: hydrogen peroxide, di-tert-butyl peroxide, benzoyl peroxide, dicumyl peroxide, cumene hydroperoxide, tert-butyl hydroperoxide, phthaloyl peroxide, bis(methanesulfonyl) peroxide, bis(trimethylsilyl) peroxide, 1,1-dihydroperoxycyclohexane, see also: peroxy acids

Whereas hydrogen peroxide is quite stable, most organic peroxides are powerful oxidants and even potentially explosive compounds. It is recommended to conduct reactions with peroxides in the fume hood behind a safety shield.

Recent Literature

The oxidative cleavage of C=C bonds adjacent to aryl and alkyl moieties was efficiently achieved with monoacetylated bishydroperoxides. Base-mediated fragmentation of monoacetylated bishydroperoxides generates singlet molecular oxygen as active oxidant in situ. All the reactions furnished the respective carbonyl compounds in good yields at room temperature within short reaction times.
D. Azarifar, Z. Najminejad, Synlett, 2013, 24, 1377-1382.

A Cu/2,2′-biquinoline catalyst mediates a benzylic C-H esterification with limiting C-H substrate. Blue-light irradiation promotes carboxylate-to-copper charge transfer, reducing resting-state CuII to CuI, which activates the peroxide to generate an alkoxyl radical hydrogen-atom-transfer species. This "photochemical redox buffering" sustains the activity of Cu catalysts in radical-relay reactions.
D. L. Golden, C. Zhang, S.-J. Chen, A. Vasilopoulos, I. A. Guzei, S. S. Stahl, J. Am. Chem. Soc., 2023, 145, 9434-9440.

An efficient I2/TBPB mediated oxidative formal [4 + 1] cycloaddition of N-tosylhydrazones with anilines represents a simple, general, and efficient approach for the construction of 1,2,3-triazoles under metal-free and azide-free conditions.
Z.-J. Cai, X.-M. Lu, Y. Zi, C. Yang, L.-J. Shen, J. Li, S.-Y. Wang, S.-J. Ji, Org. Lett., 2014,16, 5108-5111.