The degradation of tetracycline (1) by ozone in aqueous solution was investigated. High performance liquid chromatography (HPLC), UV-visible spectroscopy (UV-Vis), and total organic carbon (TOC) analyses revealed that although tetracycline was quickly consumed under this oxidative condition, it did not mineralize at all. Continuous monitoring by electrospray ionization mass spectrometry in the positive ion mode, ESI(ϩ)-MS, revealed that tetracycline (1), detected in its protonated form ([1 ϩ H] ϩ ) of m/z 445, reacted to yield almost exclusively two unprecedented oxidation products (2 and 3) via a net insertion of one and two oxygen atoms, respectively. Compound 2, suggested to be formed via an initial 1,3-dipolar cycloaddition of ozone at the C11a-C12 double-bond of 1, and Compound 3, proposed to be produced via a subsequent ozone attack at the C2-C3 double-bond of 2, were detected in their protonated forms in the ESI(ϩ)-MS, i.e.,

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