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

Norihiro Tada; Kazunori Miyamoto; Masahito Ochiai

doi:10.1248/cpb.52.1143

Notes

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

Norihiro Tada, Kazunori Miyamoto, Masahito Ochiai

Author information

Keywords: amino alcohol, iodosylbenzene, grob fragmentation, 3-hydroxypiperidine, iodane, water

JOURNAL FREE ACCESS

2004 Volume 52 Issue 9 Pages 1143-1144

DOI https://doi.org/10.1248/cpb.52.1143

Details

Abstract

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.

Corresponding author

Register with J-STAGE for free!