Oxidation of 3-hydroxypiperidines with iodosylbenzene in water: tandem oxidative Grob fragmentation-cyclization reaction.
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.
Tada
Norihiro
N
Faculty of Pharmaceutical Sciences, University of Tokushima, Tokushima 770-8505, Japan.
Miyamoto
Kazunori
K
Ochiai
Masahito
M
D003500:Cyclization; D007462:Iodobenzenes / Q000737:chemistry*; D015394:Molecular Structure; D010084:Oxidation-Reduction; D010880:Piperidines / Q000737:chemistry*; D014867:Water
D007462:Iodobenzenes; D010880:Piperidines; D014867:Water; C037276:iodosobenzene