Dibenzyl peroxydicarbonate

Dibenzyl peroxydicarbonate, (QHsCFMDCOj) (1). The reagent is obtained by reaction of benzyl chloroformate with H202 in a basic medium. It is stable to water and is not readily detonated. 

For further examples of dichotomous solvent-influenced radical/ionic perester decompositions, see the base-catalyzed perester fragmentation shown in Eq. (5-39) in Section 5.3.2 [110], as well as the decomposition of t-butyl heptafluoroperoxybutyrate, C3p7-C0-0-0-C(CH3)3 [691]. The relative extent of monomolecular and induced thermal decomposition of disubstituted dibenzyl peroxydicarbonate, ArCH2-0-C0-0-0-C0-0-CH2Ar, is also substantially influenced by the reaction medium [692]. The thermolysis of suitable dialkyl peroxides can also proceed by two solvent-dependent competitive reaction pathways (homolytic and electrocyclic reaction), as already shown by Eq. (5-59) in Section 5.3.4 [564]. 

Dibenzyl peroxydicarbonate has been used for the oxidation of both chiral and achiral lithium or potassium enolates to form carbonates of a-hydroxy carbonyl compounds. Dibenzyl peroxydicarbonate, prepared from aqueous hydrogen peroxide and benzyl chlo-roformate under basic conditions, was preferred for mechanistic studies to the commonly used MoOPH in view of the easier preparation of 0-labelled compounds . 

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