Issue 14, 1993

Regenerable N-alkylamide hydroperoxide for catalytic substrate oxidation

Abstract

The use of N-methylpyrrolidinone in a catalytic cycle employing O2 and H2 in the presence of transition metal catalysts provides a regenerative hydroperoxide system. When treated with O2 at 75 °C, N-methylpyrrolidinone is converted into the corresponding hydroperoxide, 5-hydroperoxy-1-methylpyrrolidin-2-one. This stable hydroperoxide undergoes reactions similar to those of tert-butyl hydroperoxide, yielding N-methylsuccinimide as the product. By using either heterogeneous or homogeneous catalysts, N-methylsuccinimide can be reduced with H2 under mild conditions to the hydroperoxide precursor, N-methylpyrrolidinone. The steps in the conversion of the hydroperoxide into N-methylsuccinimide were elucidated by study of the oxidation of PPh3 to OPPh3. Oxygenatom transfer from the hydroperoxide to the phosphine produces the amido alcohol intermediate, 5-hydroxy-1-methylpyrrolidin-2-one. In the presence of O2, the amido alcohol intermediate undergoes rapid oxidation to N-methylsuccinimide.

Article information

Article type
Paper

J. Chem. Soc., Perkin Trans. 1, 1993, 1611-1615

Regenerable N-alkylamide hydroperoxide for catalytic substrate oxidation

D. E. Patton and R. S. Drago, J. Chem. Soc., Perkin Trans. 1, 1993, 1611 DOI: 10.1039/P19930001611

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