Nonstabilised azomethine ylids from N-oxides: unravelling the deprotonation of N-methylmorpholine N-oxide

Paul Malek Mirzayans, Elizabeth H. Krenske, Craig M. Williams*

*Corresponding author for this work

Research output: Contribution to journalArticlepeer-review

5 Citations (Scopus)


Nonstabilised azomethine ylids (NAYs) are useful 1,3-dipoles, but their synthetic applications are restricted by the high temperatures often needed for their generation, and by an incomplete understanding of the effect of heteroatoms in cyclic systems. We have examined the behaviour of N-methylmorpholine N-oxide (NMO) as a NAY precursor in the Roussi reaction (low-temperature reaction of an N-oxide with strong base). The choice of base is critical to achieving cycloadduct formation. We report synthetic and computational (density functional theory) investigations of the products obtained with different bases and their mechanisms of formation.

Original languageEnglish
Pages (from-to)1309-1317
Number of pages9
JournalAustralian Journal of Chemistry
Issue number9
Publication statusPublished - 4 Jun 2014
Externally publishedYes

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