Peroxides
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.
