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RESEARCH ARTICLE
Contents Vol 67(9)

Nonstabilised Azomethine Ylids from N-Oxides: Unravelling the Deprotonation of N-Methylmorpholine N-Oxide

Paul Malek Mirzayans A , Elizabeth H. Krenske A and Craig M. Williams A B
+ Author Affiliations
- Author Affiliations

A School of Chemistry and Molecular Biosciences, University of Queensland, Brisbane, Qld 4072, Australia.

B Corresponding author. Email: c.williams3@uq.edu.au

Australian Journal of Chemistry 67(9) 1309-1317 https://doi.org/10.1071/CH14217
Submitted: 4 April 2014  Accepted: 7 May 2014   Published: 4 June 2014

Abstract

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.


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