Synlett 2013; 24(16): 2175-2176
DOI: 10.1055/s-0033-1338973
© Georg Thieme Verlag Stuttgart · New York

N-Methylmorpholine N-Oxide

Tanya Pieterse
Department of Chemistry, Faculty of Natural and Agricultural Science, University of the Free State, P.O. Box 339, Bloemfontein 9330, South Africa   Email:
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Publication History

Publication Date:
26 August 2013 (online)


N-Methylmorpholine N-oxide [NMMO (2)] is a light yellow powder with a melting point of 180–184 °C.[1] It is commercially available in both the monohydrate (C5H11NO2·H2O) and anhydrous forms, and is stable under normal conditions.

Apart from being a powerful environmentally friendly solvent for dissolving cellulose,[2] [3] NMMO (2) acts as a strong oxidizing agent and is generally utilized as a stoichiometric oxidant together with TPAP and OsO4 for hydroxy group oxidation[4] and dihydroxylation of olefins.[5] [6]

The oxidative dehydrogenation of amines utilizing gold as the catalyst is also carried out in the presence of NMMO (2), where it acts as a base to afford imines in good yield.[7]

Moreover, NMMO (2) can react as a nucleophile, as is displayed during the reductive work-up of ozonolysis intermediates to afford aldehyde products.[8] [9] One of the advantages of using NMMO versus oxidants like hydrogen peroxide is found in the fact that the byproduct after oxidation [NMM (1)] is very low in basicity.

  • References

  • 1 Wilson, C. A.; Honors Thesis, The Florida State University, USA, 2013.
  • 2 Fink H.-P, Weigel P, Purz HJ, Ganster J. Prog. Polym. Sci. 2001; 26: 1473
  • 3 Dogan H, Hilmioglu ND. Carbohydr. Polymers 2009; 75: 90
  • 4 Mehta G, Pan SC. Org. Lett. 2004; 6: 811
  • 5 Krishna PR, Reddy PS. Synlett 2009; 209
  • 6 de la Fuente MC, Castedo L, Domínguez D. J. Org. Chem. 1996; 61: 5818
  • 7 Klobukowski ER, Angelici RJ, Woo LK. Catal. Lett. 2012; 142: 161
  • 8 Schwartz C, Raible J, Mott K, Dussault PH. Tetrahedron 2006; 62: 10747
  • 9 Pieterse T.; M.Sc. Thesis, University of the Free State, Bloemfontein, S.A., 2013.
  • 10 Youssif S. ARKIVOC 2001; (i): 242
  • 11 Schwartz C, Raible J, Mott K, Dussault PH. Org. Lett. 2006; 8: 3199