Oxidation of 3-Hydroxypiperidines with Iodosylbenzene in Water: Tandem Oxidative Grob Fragmentation-Cyclization Reaction

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Oxidation of 3-hydroxypiperidine with iodosylbenzene in water afforded 2-pyrrolidinone directly in good yields. The reaction probably involves oxidative Grob fragmentation yielding imino aldehyde, which upon hydrolysis produces 2-pyrrolidinone via a cyclization–oxidation sequence.

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