2 added 31 characters in body edited Feb 23 '15 at 2:31 ron 73.2k1010 gold badges161161 silver badges267267 bronze badges N-methyl-morpholine-N-oxide (NMO) is used to reoxidize and regenerate osmium tetroxide ($$\ce{OsO4}$$) in what is known as the "Upjohn Dihydroxylation" procedure. Mechanistically, the redox occurs when a lone pair of electrons on the reduced $$\ce{OsO3}$$$$\ce{Os(VI)O3}$$ are used to form a bond to the morpholine N-oxygen; the electrons from the former $$\ce{N-O}$$ bond are, in turn, transferred to the morpholine nitrogen. The $$\ce{OsO3}$$ gains an oxygen and is oxidized back to osmium (VIII) tetroxide and the NMO is reduced to N-methylmorpholine image source Osmium tetroxide is both toxic and expensive. Using the Upjohn procedure allows the reaction to be run with a catalytic amount of osmium teroxide and 1 equivalent of NMO. N-methyl-morpholine-N-oxide (NMO) is used to reoxidize and regenerate osmium tetroxide ($$\ce{OsO4}$$) in what is known as the "Upjohn Dihydroxylation" procedure. Mechanistically, the redox occurs when a lone pair of electrons on the reduced $$\ce{OsO3}$$ are used to form a bond to the morpholine N-oxygen; the electrons from the former $$\ce{N-O}$$ bond are, in turn, transferred to the morpholine nitrogen. The $$\ce{OsO3}$$ is oxidized back to osmium tetroxide and the NMO is reduced to N-methylmorpholine image source Osmium tetroxide is both toxic and expensive. Using the Upjohn procedure allows the reaction to be run with a catalytic amount of osmium teroxide and 1 equivalent of NMO. N-methyl-morpholine-N-oxide (NMO) is used to reoxidize and regenerate osmium tetroxide ($$\ce{OsO4}$$) in what is known as the "Upjohn Dihydroxylation" procedure. Mechanistically, the redox occurs when a lone pair of electrons on the reduced $$\ce{Os(VI)O3}$$ are used to form a bond to the morpholine N-oxygen; the electrons from the former $$\ce{N-O}$$ bond are, in turn, transferred to the morpholine nitrogen. The $$\ce{OsO3}$$ gains an oxygen and is oxidized back to osmium (VIII) tetroxide and the NMO is reduced to N-methylmorpholine image source Osmium tetroxide is both toxic and expensive. Using the Upjohn procedure allows the reaction to be run with a catalytic amount of osmium teroxide and 1 equivalent of NMO. 1 answered Feb 22 '15 at 20:21 ron 73.2k1010 gold badges161161 silver badges267267 bronze badges N-methyl-morpholine-N-oxide (NMO) is used to reoxidize and regenerate osmium tetroxide ($$\ce{OsO4}$$) in what is known as the "Upjohn Dihydroxylation" procedure. Mechanistically, the redox occurs when a lone pair of electrons on the reduced $$\ce{OsO3}$$ are used to form a bond to the morpholine N-oxygen; the electrons from the former $$\ce{N-O}$$ bond are, in turn, transferred to the morpholine nitrogen. The $$\ce{OsO3}$$ is oxidized back to osmium tetroxide and the NMO is reduced to N-methylmorpholine image source Osmium tetroxide is both toxic and expensive. Using the Upjohn procedure allows the reaction to be run with a catalytic amount of osmium teroxide and 1 equivalent of NMO.