Morpholine 4-methyl-4-oxide

N-Methylmorpholine N-oxide monohydrate Morpholine, 4-methyl-, 4-oxide, monohydrate (8,9), ( —)... 

Iminium + R —COONa) Morpholin 4-Methyl- -4-oxid Vl/la, 1, 607 Pentan... 

Methylmorpholine N-oxide Morpholine, 4-methyl-, 4-oxide (8,9) 7529-22-8) Dihydroquinidine 4-chlorobenzoate Cinchonan-9-ol, 10,11-dihydro-6 -methoxy-, 4-chlorobenzoate (ester), (9S)- (12) (113162-02-0)... 

Morpholine, 4-coco alkyl derivs, 4-oxides. See Coco-morpholine oxide Morpholine, 4-methyl-. See p-Methyl morpholine Morpholine, 4-methyl-, 4-oxide. See Methyl morpholine oxide Morpholine, 4-(1-oxoisooctadecyl)-, salt with octadecanoic acid. See Isosteara-midomorpholine stearate... 

Methylthiopyrido[2,3-e][ 1,2,4]triazine 41 was prepared (76KGSI140) by cyclization of 2-amino-3-hydrazinopyridine 40 with carbon disulfide followed by methylation. Oxidation of 41 with chlorine afforded the 3-methylsulfonopyridotriazine 42. Heating 41 with morpholine or pyrrolidine gave 43, whereas the reaction at 20°C gave 44. 

Newcell A process for making reconstituted cellulose fibers by dissolving cellulose in N-methyl morpholine N-oxide and injecting the solution into water. Invented in 1977 by Akzona, NC. 

Acyl nitroso compounds react with 1, 3-dienes as N-O heterodienophiles to produce cycloadducts, which have found use in the total synthesis of a number of nitrogen-containing natural products [21]. The cycloadducts of acyl nitroso compounds and 9,10-dimethylanthracene (4, Scheme 7.3) undergo thermal decomposition through retro-Diels-Alder reactions to produce acyl nitroso compounds under non-oxidative conditions and at relatively mild temperatures (40-100°C) [11-14]. Decomposition of these compounds provides a particularly clean method for the formation of acyl nitroso compounds. Photolysis or thermolysis of 3, 5-diphenyl-l, 2, 4-oxadiazole-4-oxide (5) generates the aromatic acyl nitroso compound (6) and ben-zonitrile (Scheme 7.3) [22, 23]. Other reactions that generate acyl nitroso compounds include the treatment of 5 with a nitrile oxide [24], the addition of N-methyl morpholine N-oxide to nitrile oxides and the decomposition of N, O-diacylated or alkylated N-hydroxyarylsulfonamides [25-29]. 

IV-Methylmethanesulfonamide, 23 685 IV-Methyl morpholine-AT-oxide (NMMO) as cellulose solvent, 11 266, 267, 268 environmental issues related to,... 

TPA-Ru04 (4.5 mg, 0.013 mmol) is added to the nitro compound (0.13 mmol), A-methyl-morpholine-iV-oxide (22.7 mg, 0.194 mmol), AgOAc (43 mg, 0.258 mmol), K2CO, (90 mg, 0.65 mmol) and powdered 4A molecular sieves (0.1 g) in MeCN (2 ml). The mixture is stirred for 10 h at 40° C and Et20 (5 ml) is then added. Filtration through Celite and evaporation of the filtrate yields the ketone. 

The oxidation of alcohols to carbonyl compounds has been studied by several authors and a variety of methods have been used. Papers concerned vith such oxidations are illustrated (Scheme 3.26). Good results have been obtained using pyridinium chlor-ochromate (PCC) adsorbed onto silica gel for the selective oxidation of unsaturated substrates e.g. terpene [135] and furanyl derivatives [136]. Steroidal homoallylic alcohols can be converted to the corresponding 4-ene-3,6-diones using tetrapropylammo-nium per-ruthenate (TPAP) in catalytic amounts [137]. In this case, the oxidising agent is N-methyl morpholine N-oxide (NMO). 

Chanzy and Peguy (13) were the first to report that cellulose forms a lyotropic mesophase. They used a mixture of N-methyl-morpholine-N-oxide (MMNO) and water as the solvent. Solution birefringence occurred at concentrations greater than 20% (w/w) cellulose. The concentration at which an ordered phase formed increased as the cellulose D.P. decreased. The persistence length of cellulose in MMNO-H2O is not known but presumably it has an extended chain configuration in this solvent. Again the question arises as to what is the relevant axial ratio to be used for cellulose. This will be discussed further below. 

A more recent process for producing regenerated cellulose involves the use of V-methyl-morpholine-A-oxide, a highly polar solvent, at about 130°C to dissolve cellulose [Rosenau et al., 2001], About 5% of all regenerated cellulose is produced by this method. 

Tb a solution of 7 (458 mg, 1.7 mmol) and /V-methyl morpholine /7-oxide (244 mg) in r-butanol (1 mL), a few crystals of osmium tetraoxide dissolved in THF (1.5 mL) were added. After 3 days 40% aqueous solution of NaHS03 (3 mL) was added, the mixture was stirred for additional 30 min, and extracted with ethyl acetate (3 x 20 mL). The extracts were dried (MgS()4) and concentrated to dryness. The residue was purified by chromatography on a silica gel column with light petroleum-ether-methanol (4 5 0.5) to yield 9 (371 mg, 72%) mp 89.5° (from a mixture of hexane and ethyl acetate), [a]D + 52° (c 1.0, CHClj). 

Osmium tetroxide-N-Methyl-morpholine N-oxide, 222 Osmium tetroxide-Trimethylamine N-oxide-Pyridine, 223 Palladium Compounds Benzylchlorobis(triphenylphosphine)-palladium(II), 30 Bis (ace tonitrile) chloronitropalla-dium(II)-Copper(II) chloride, 33 Bis(acetonitrile)dichloropalladium(II), 33, 211, 236... 

A milestone in the routine employment of perruthenate in the oxidation of alcohols was established with the publication by Griffith, Ley et al. in 1987 on the catalytic use of tetra- -propylammonium perruthenate (TPAP).11 The presence of the tetra- -propylammonium cation renders this compound soluble in apolar media and allows the existence of a high concentration of perruthenate ion in organic solvents. The tetra- -propylammonium perruthenate is easily prepared and can be employed catalytically in CH2CI2 solution in the oxidation of alcohols to ketones and aldehydes, using /V-methyl morpholine A-oxide (NMO) as the secondary oxidant. 

R)-isomer in a reaction where chirality was transferred from a (R)-ct-phenyl methyl substituent at N-4 <2004TA687>. The imine double bond of a l,4-diazepin-5-one can be introduced by oxidation of the saturated amine using tetra- -propylam-monium perruthenate (TPAP) and A -mcthyl morpholine /V-oxide (NMO), as the co-oxidant <1997T3223>. 

The Upjohn Dihydroxylation allows the sy/i-selective preparation of 1,2-diols from alkenes by the use of 0s04 as a catalyst and a stoichiometric amount of an oxidant such as NMO (N-methyl morpholine- JV-Oxide). 

Oxidation of alcohols. Griffith and Ley1 report various improvements for use of this reagent for catalytic oxidation of alcohols in combination with N-methyl-morpholine N-oxide as reoxidant. In general, the yields with this oxidant are higher than those obtained by the Swern reagent. 

Fig. 4. Danishefsky s total synthesis formation of cyclobutanone, sulfenylation, and successive oxidation reactions. DME = 1,2-dimeth-oxyethane, TBAF = tetra-n-butylammonium fluoride, NMO = A/-methyl-morpholine-N-oxide.

TPAP = Tetrapropylammonium perruthenate DMAP = 4-dimethylaminopyridine. NHO = N-methyl morpholine N-oxide ... 

Marsano, E., Corsini, P., Arosio, C., Boschi, A., Mormino, M., and Freddi, G. "Wet spinning of Bombyx mori silk fibroin dissolved in N-methyl morpholine N-oxide and properties of regenerated fibres". Int. J. Biol. Macromol. 37(4), 179-188 (2005). 

A one-sided binding of the complex to the support resulted in further improvements (92). This requires synthesis of nonsymmetric salen-type ligands, which is complicated by the tendency of such ligands to equilibrate to give mixtures containing symmetric Schiff bases. Excellent results were obtained with monomer 7d, diluted in a methacrylate polymer, by using a combination of meta-chloroperbenzoic acid (mCPBA) and A-methyl-morpholine-A-oxide (NMO) as the oxidants ... 

Alceru [Alternative cellulose Rudolstadt] A process for making cellulosic filaments and staple fibers. The cellulose is first dissolved in an aqueous solution of N-methyl morpholine N-oxide (NMMNO) and then spun. Developed by the Thiiringische Institut fur Textil- and Kunstoff-Forschung e.V. Rudolstadt, Germany, and Zimmer (Frankfurt) from 1987. A pilot plant was built in April, 1998 and a commercial plant was planned for installation in Baoding, China in 2005. A superabsorbent version of the fiber has been developed by Stockhausen. The fiber is now made commercially by Sea Cell GmbH, a subsidiary of Zimmer. See also Lyocell. 

A very broad class of primary oxidants act as oxygen atom transfer agents, the most widely nsed oxidants in oxidation catalysis. These inclnde peracids or their anion forms, snch as MCPBA or oxone (O-OSOs ) as well as A-oxides snch as A-methyl morpholine A-oxide or hypochlorite ion. They all have general structure XO, where X is a good leaving gronp. 

Another ruthenium-catalyzed oxidation uses tetrapropylammonium permthenate (TRAP) [24]. Being a ruthenium(VII) oxide, the permthenate ion is a less powerful oxidant than rutheni-um(VIII) oxide and more functional groups are stable to the oxidation conditions, including alkenes, alkynes, amines, amides, benzyl, trityl and silyl ethers [24]. However, alcohols and lactols still undergo oxidations in high yield with W-methyl-morpholine A-oxide (NMO) as the stoichiometric oxidant. The reactions are usually carried out in dichloromethane, acetonitrile, or mixtures of both in the presence of molecular sieves [24]. 

The chiral directing groups are pinanediols derived from osmium tetroxide-cat-alyzed oxidation of either (+)-a-pinene or (-)-a-pinene with trimethylamine oxide or with NMO (N-methyl-morpholine-N-oxide). The (s) and (r) notations shown in the abbreviations refer to the configuration of the chiral center in the a-chloroboronic ester using the appropriate pinanediol. 

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