Attempted Synthesis and Unexpected β-Fragmentation of a Hindered β-Keto Nitroxide | Zendy

Chris Edwards | Zendy; Peter C. Healy | Zendy; W. Ken Busfield | Zendy; Ezio Rizzardo | Zendy; San H. Thang | Zendy; Ian D. Jenkins | Zendy

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Attempted Synthesis and Unexpected β-Fragmentation of a Hindered β-Keto Nitroxide

Author(s) -

Chris Edwards,

Peter C. Healy,

W. Ken Busfield,

Ezio Rizzardo,

San H. Thang,

Ian D. Jenkins

Publication year - 2017

Publication title -

australian journal of chemistry

Language(s) - English

Resource type - Journals

SCImago Journal Rank - 0.319

H-Index - 77

eISSN - 1445-0038

pISSN - 0004-9425

DOI - 10.1071/ch17203

Subject(s) - chemistry , hydrogen peroxide , sodium tungstate , fragmentation (computing) , supramolecular chemistry , reaction mechanism , biocatalysis , nitroxide mediated radical polymerization , ring (chemistry) , yield (engineering) , medicinal chemistry , green chemistry , macromolecule , catalysis , crystal structure , organic chemistry , materials science , tungsten , metallurgy , operating system , biochemistry , polymer , radical polymerization , copolymer , computer science

The attempted synthesis of a β-keto imidazolidinone nitroxide by oxidation of the β-hydroxy imidazolidinone precursor with hydrogen peroxide and sodium tungstate led to an unexpected ring-opening reaction to produce 1,4-diazaspiro[4.5]dec-1-en-3-oxo-2-pentanoic acid 1-oxide (13) in high yield. The structure of 13 was confirmed by X-ray crystallographic analysis. A β-fragmentation mechanism is suggested for the oxidative ring-opening reaction.Griffith Sciences, School of Natural SciencesFull Tex

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