26 August 2013 (online)
N-Methylmorpholine N-oxide [NMMO (2)] is a light yellow powder with a melting point of 180–184 °C. 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,  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 and dihydroxylation of olefins. 
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.
Moreover, NMMO (2) can react as a nucleophile, as is displayed during the reductive work-up of ozonolysis intermediates to afford aldehyde products.  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.
- 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