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N-Hydroxyphthalimide derivatives, F15- and F17-NHPI, bearing fluorinated carboxylate and alkyl chains, respectively, were prepared and their catalytic performances were compared with those of N-hydroxyphthalimide (NHPI). Thus, the oxidation of cyclopentane under 10 atm of air in the presence of catalytic amount of fluorinated NHPI or NHPI, Co(OAc)2, and Mn(OAc)2 in TFT as solvent at 100°C afforded cyclopentanol, cyclopentanone, succinic acid and glutaric acid. It was assumed that F-NHPI derivatives bearing electron withdrawing fluorocarbon groups showed higher catalytic activity than the NHPI by enhancement of the electrophilicity of N-oxy radicals generated from the F-NHPI derivatives. In the oxidation of cyclopentane, F-NHPI showed better catalytic activity than NHPI. Cyclopentanol and glutaric acid were obtained as the major products in case of NHPI, whereas, cyclopentanone and glutaric acid were obtained as the major products in case of fluorinated NHPIs. However, only glutaric acid was obtained as the major product when a increased amount of Co(OAc)2 was used in the present ocidation by using NHPI or F-NHPIs. The effect of temperature and air was also investigated in the oxidation of cyclopentane. When the oxidation was performed at 90°C, cyclopentanol was obtained as the major product, whereas, no significant changes were observed when the reaction was performed at 20 atm instead of 10 atm. The great advantage of the fluorinated NHPI derivatives is that it could be recovered after the oxidation.

Aerobic Oxidation of Cyclopentane by Using Fluorinated &lt;I&gt;N&lt;/I&gt;-Hydroxyphthalimide Derivatives

Aerobic Oxidation of Cyclopentane by Using Fluorinated <I>N</I>-Hydroxyphthalimide Derivatives