N, O-dimethylhydroxylamine

O, N-Dimethylhydroxylamine. Diphenyl phosphoroazidate. lodosylbenzene. Sodium bis(trimethylsilyl)amide. Sodium hydrogen telluride. Triphenylphosphine. 

FIGURE 7.2 NMR spectrum showing the large influence of coordination of S-containing heteroligands on 51V chemical shifts compared to similar O coordinated ligands in bis(N,N-dimethylhydroxylamine)(heteroligand)vanadium(V) complexes at pH 8.50. Experimental conditions total vanadate, 5.0 mM total Af.AI-di methyl hydroxylamine, 40 mM total cysteine, 90 mM KC1, 1.0 M pH, 8.5. 

O - () - Hydroxy ethyl) - N,N - dimethylhydroxylamine methiodide and KOH in methanol heated to boiling, the product distilled together with most of the methanol, and the distillate treated with picric acid trimethylamine picrate. Y ca. 76%. F. e. s. B. J. R. Nicolaus, G. Pagani, and E. Testa, Helv. 45, 358 (1962). 

Esters ofN,N-dialkylhydroxylamines ((acyloxy)amines) appear to be possible candidates for prodrugs of carboxylic acids, but more studies must be published before any firm conclusion can be drawn. First, there are indications of low acute toxicity for N,N-(1 al ky I hydroxy Iambics [87], Whether the same applies (acutely and chronically) to the pro-moieties after their release from the prodrugs is not known. A second argument is the low basicity of hydroxylamines (the pKa of Ar,AT-dimethylhydroxylamine is 5.2), and the expected lower basicity of O-acylatcd hydroxylamines. As a result, esters of hydroxylamines will be in the unprotonated, more lipophilic form at physiological pH and should be absorbed more readily than the corresponding carboxylic acid [88]. 

Engelhard , G., Wallnofer, P.R., and Plapp, R. Identification of N, O-dimethylhydroxylamine as a microbial degradation product of the herbicide, linuron, Appl Microbiol, 23 664-666, 1972. 

Horner-Emmons reaction of N-terminal blocked aldehyde 1 with sulfonylphosphonates in the presence of sodium hydride gives the amino acid vinyl sulfone 2, which is deprotected with acid and converted into its chloride or tosylate salt 3 and coupled by the mixed anhydride method with an N-terminal protected peptide or amino acid to give the desired peptide vinyl sulfones 4 (Scheme 2). 4 5 N-Terminal protected aldehydes 1 are obtained from reduction of Boc amino acid V-methoxy-A-methylamides (Weinreb amides, see Section 15.1.1) by lithium aluminum hydride. 9 The V-methoxy-V-methylamide derivatives are prepared by reaction of Boc amino acids with N,O-dimethylhydroxylamine hydrochloride in... 

ALDEHYDES Acetone cyanohydrin. Dichlorobis(cyclopentadienyl)titanium(II). Diisobutylaluminum hydride. Dimethylformamide. N,0-Dimclhylhydroxylamine hydrochloride. 4-Eormyl-l -methylpyridinium hcnzcncsuifonatc. N-Formylpiperidine. N.O-Dimethylhydroxylamine hydrochloride. 2-(2,6-l)imethylpipcridino)aectonitrile Mclhoxy(triniclhyl.silyl)incihyl lidiiiim... 

KETONES N.O-Dimethylhydroxylamine hydrochloride. N,N,-Diphenyl-/>-mcthoxyphenylchloromethyleniminum chloride. Formaldehyde dimethyl dithioacetal S.S-dioxidc 4-Fonmyl l methylpyridiniuni bcnzencsullonatc. l.ithi[Pg.651]

We studied this reaction by calorimetry and found that the addition of triisobutylaluminum to a suspension of N, O-dimethyl-hydroxylamine hydrochloride in THF was highly exothermic. It was also noted that the resulting complex of triisobutylaluminum/A, O-dimethylhydroxylamine /THF was thermally unstable. According to differential scanning calorimetry, this complex started to exothermically decompose at 30 °C and reached the maximum exotherm at 140 °C, resulting in the release of a total of -406 kJ/kg of heat. This instability is presumably due to an aluminum-catalyzed polymerization reaction of tetrahydrofuran. Thus,... 

Boa-L-Leuoine N-msthyl-O-methyloarboxamide. A 1-L, three-necked, round-bottomed flask is equipped with a mechanical stirrer, an electronic digital thermometer, and a graduated addition funnel. The flask is charged with 39.1 g (0.4 mol) of N,0-dimethylhydroxylamine hydrochloride (Note 1) and 236 mL of methylene chloride (Note 2). The suspension is stirred and cooled to 2°C with an ice-water bath. N-Methylpiperidine (Note 3), 48.8 ni. (0.41 mol), is placed in the addition funnel and added dropwise while the temperature is maintained at 2° + 2°C. A clear, colorless solution results which is kept cold and used in the following reaction. 

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