Copper(II)-catalyzed aerobic oxidation of indane in the presence of aldehydes: intermediate formation of hydroperoxides

Indane reacts with oxygen, at room temperature, in the presence of isobutyr aldehyde, and a copper(II) derivative (Cu(OH)(2), CuCl2, Cu(TPIP)(2)) to gi ve a mixture of indan-1-yl hydroperoxide and indanone, together with small amounts of indanol. In the presence of Tempo or diphenylamine, as radical s cavengers, no reaction takes place. Thus, no direct formation of indanol, a s precursor of indanone, via metal-oxo derivatives is likely to occur. The ratio hydroperoxide/indanone is highly dependent on the nature of the trans ition metal in TPIP-derived complexes. (C) 2000 Elsevier Science B.V. All r ights reserved.