Synthesis of 14C-labeled cyclic peroxide, 4-ethoxy-2,3-benzodioxin-1-ol, and its decomposition

Synthesis of 14C-labeled 4-cthoxy-2, 3-benzodioxin-1-ol (EtO-BD) from [1(4,5,8)-14C]naphthalene and the decomposition behavior of the labeled EtO-BD are described. 14C-EtO-BD is stable over months as long as kept at -40degC as a solid state, and over weeks in acetonitrile. The decomposition of EtO-BD is facilitated by the presence of H2O giving rise to two major decomposition products, o-phthalaldehydic acid and its ethyl ester. Thus the generation of OH radical is expected on its decomposition path and is enhanced as increasing H2O concentration. Fe(II) seems to facilitate EtO-BD decomposition through the electron transfer reaction.(author)