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

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

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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.

Original languageEnglish
Pages (from-to)1106-1109
Number of pages4
JournalAustralian Journal of Chemistry
Issue number10
Publication statusPublished - 31 May 2017
Externally publishedYes

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