A series of substituted N-hydroxyphthalimides (NHPI) with electron-withdrawing groups (4-C(O)OH, C=O) and an electron-donating group (4-C(CH3)3) were investigated as catalysts for cumene oxidation. The initial reaction rates, measured by the oxygen uptake, conversion of substrate and yield of oxidation products are discussed. The catalytic activity of oxidation rate enhancement of NHPI derivatives in acetonitrile follows the order 4-tert-BuNHPI > NHPI > 4-carb-NHPI > NDHPI > NAPI. NMPT, trityl-NPI and NHPLI are inactive.
Ishii, Y, Nakayama, K, Takeno, M, Sakaguchi, S, Iwahama, T, Nishiyama, Y (1995) J Org Chem. 60:3934.