Amine oxides oxidation with

The performance potential of synergistic mixtures of anionics (e.g., alkanesulfonates) and amine oxides with hydroxyethylene groups was already analyzed some years ago [89]. It was shown that lauryldi(hydroxyethylene)amine N-oxide lowers the Zein values of the mixtures with alkanesulfonates. 

Complexes of the lanthanides with amine oxides, nitroso compounds, and nitroxide radicals fall under this category. However, only the complexes with the amine oxides have received wide attention. Four comprehensive reviews have appeared on the complexes of amine oxides with various metal ions 142-145). Only a few complexes of the lanthanides have been quoted in these reviews. 

Complexes of monodentate aliphatic amine oxides with the lanthanides have not been extensively investigated. The only series of complexes with a ligand of this type, Et3NO, has been reported by Pavlenko et al. (181). The complexes have the formula [Ln(Et3N0)6][Cr(NCS)6]-2H20. 

The reaction of tertiary amine oxides with nitrous acid has also been shown to produce N-nitroso compounds. The mechanism for the amine oxides is similar to that for the tertiary amines (26). 

The second factor, namely the head group interaction, can also influence the surface properties of mixed surfactant markedly. In particular, anionic/catlonic surfactant mixtures exhibit the largest effect (17,18). In nonionic/anionic surfactant mixtures, synergistic effects can still take place to a significant extent, as revealed in Figure 3 (pH 10.9, nonionic amine oxide with anionic long chain sulfate), since insertion of nonionic surfactant molecules into an ionic surfactant molecular assembly minimises electrostatic repulsion (19). 

When the unsaturated tertiary amine, pitprofen (179 R = H) is treated with MCPBA the reaction takes place selectively at the mwe nucleophilic nitrogen to furnish the corresponding amine oxide with the alkene moiety intact. In contrast, peroxycarboximidic acid, prepared in situ from acetonitrile/H202. reacts selectively with the alkene moiety of the ester (179 R = Me equation 65). The sterically hindered nitrogen of (179) is able to react with peroxy acids which have a low steric demand, but not with peroxy-caiixrximidic acids which have a large steric demand. 

Tertiary amine oxides with three different substituents exist as stable enantiomers8. Pure enantiomers were obtained by resolution. Asymmetric oxidation of tertiary amines usually gave amine oxides with low enantioselectivity8. Oxidation of Ar-(/f)-2-butcnyl-Ar-methyl-4-toluidine... 

In several instances reaction of an amine oxide with an acid anhydride triggers a process in which the amine oxide nitrogen is converted into a leaving group and the Co—bond is cleaved (Scheme 15). ° Interestingly, these reactions occur to the exclusion of the Polonovski pathways, i.e. elimination of the benzylic a-hydrogen or fragmentation of the phenethylamine chain. 

The heading production of chemical products includes the conversion of allyl alcohol to glycerine with hydrogen peroxide, the production of epoxy-compounds such as epoxy soya oil (plasticizer for PVC) and organic peroxides (e.g. methyl-ethyl-ketone-peroxide, dibenzoylperoxide), which are used as free radical initiators in polymerization processes. The production of amine oxides such as lauryl-dimethyl-amine-oxide with hydrogen peroxide (used as a rinsing agent in dishwashers) is also included. 

U.S. 4,259,216 (1981) Miyajima et al. (Lion) a-Olefin sulfonate, alkylethoxy sulfate, and alkyl amine oxide with aryl sulfonate No hand roughening and good for vegetables... 

Deoxygenation. Removal of the oxygen atom from amine oxides with the mixed anhydride at the temperature of ice is quite convenient. The mixed anhydride is formed and used in situ from HCOONa and pivaloyl chloride. 

Trifluoroethylidenation of activated CH2P The Polonovski reaction of dimethyl(trifluoroethyl)amine oxide with (CFjCOljO in the presence of a compound containing an active methylene group accomplishes trifluoroethylidenation at that site. 

Mild amine oxide with hydroxyethyl groups in the polar moiety can be also produced by oxidation of ethoxylated fatty amine. 

The mild oxidizing properties of IBX enhance its utility for the oxidation of compounds with sensitive functional groups such as thioethers and amines. Oxidation with IBX occurs cleanly in the presence of thioethers and 1,3-dithiolane protecting groups. For exan5)le, oxidation of thiochroman-4-ol, even with 10 equiv of IBX is achieved cleanly to give thiochroman-4-one with no detection of the analogous sulfoxide or sulfone by-products (eq 2). ... 

As with betaines and other amphoterics, efforts continue in the development of amine oxides with reduced levels of residual impurities. A process for preparing long monoalkyl-chain amine oxides with low nitrite and nitrosamine levels [41] and another process [42] involving the oxidation of Cjg-Cig dimethylamine with hydrogen peroxide in the presence of malic acid and diethylenetriaminepentaacetate (DTPA) have been described. The resulting amine oxide contains (the undesired) nitrite levels below 1 ppm [42]. 

The sulphurdi-imines are hydrolysed in acidic media to sulphur dioxide and two equivalents of amine. Oxidation with ozone afforded a nitrocompound and sulphinylamine. Pyrolysis of the diphenyl derivative (100 R = Ph) gave azobenzene, but pyrolysis of the di-t-butyl derivative (100 R = t-butyl) resulted in an intramolecular elimination to isobutylene, hydrogen sulphide, and ammonia. The bis-tosyl imine (100 R = toluene-p-sulphonyl) reacted with diamines (1,2----------1,6-) in an... 

When an amine oxide with at least one j8-hydrogen is heated, it undergoes thermal decomposition to form an alkene and an N,N-dialkylhydroxylamine. Thermal decomposition of an amine oxide to an alkene is known as a Cope elimination after its discoverer Arthur C. Cope of the Massachusetts Institute of Technology. 

The cleavage of amine oxides with acylating agents gives aldehydes and acylated secondary amines in good yield (equation 47) . The... 

An interesting by-product of this study was some insights into the effect of multiple ether linkages in the molecule on interfacial properties and interactions with other surfactants [13]. The molecules under investigation have the structures shown in Fig. 3. Those with multiple ether linkages in the molecule showed a smaller increase in their interaction with an amine oxide with a decrease in the pH of the system than molecules without multiple ether linkages. Data are shown in Table 8. 

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