Oxidizing Reagent

1 is a convenient, stable, and recyclable oxidizing agent, particularly useful in oxidizing allylic alcohols, as in the synthesis of geranial 3 from geraniol 2,¹⁾ and the oxidation of hemiacetal 5, such as an aldose sugar, into aldonolactone 6.²⁾ Byproduct 4 can be oxidized using sodium hypochlorite and recycled back into 1 for reuse. It can also be used to transform bifunctional alcohol 7 into ester 8 by oxidative dimerization³⁾ and in the synthesis of allylic alkoxyamines.⁴⁾