Propane 2-methyl-2-nitroso

Alkyl and aryl C-nitroso compounds contain a nitroso group (-N=0) directly attached to an aliphatic or aromatic carbon. As compounds with a nitroso group attached to a primary or secondary carbon exist primarily as the oxime tautomer, the stable examples of C-nitroso compounds contain nitroso groups attached to tertiary carbons, such as 2-methyl-2-nitroso propane (1, Fig. 7.1) or nitroso groups attached to carbons bearing an electron-withdrawing group (-CN, -N02, -COR, -Cl, -OAc, Fig. 7.1). Oxidation of alkyl and aryl hydroxylamines provides the most direct route to alkyl and... 

A rapid protonation by water of the electron adducts of spin traps such as DMPO or 2-methyl-2-nitroso-propane yields the same species as are expected for the reaction of H" (Sargent and Gardy 1975). This prevents a distinction between eaq and 11 by using this technique. 

Vinylaminyloxides 48 could be obtained by treatment of 2-methyl-2-nitroso-propane with lithium vinyl compound 476S In contrast to the intermediate vinyl-aminyloxide 40, 48 is prevented from secondary reactions apparently by the small spin density at the /5-carbon atom, which is caused by the strong twisting of the N-C bond. 

Sulfamethoxazole failed to produce any trappable radicals with an array of different spin traps, but naproxen afforded the EPR spectrum shown in Figure 2.11 when irradiated with 330 nm UV-R in the instrument cavity in the presence of 2-methyl-2-nitroso-propane (MNP). The spectrum contains contributions from di-t-butyl nitroxide, a known photoproduct of MNP. The H-atom adduct MNP-H also evident can arise by several different mechanisms, including the trapping of an H atom by MNP the reaction of MNP with an electron followed by protonation and the direct reduction of MNP by an excited state species. In view of the flash photolysis results, it was concluded that photoionization was the major precursor of MNP-H. The third radical corresponded to a C-centered radical carrying a single H atom, leading to the postulate of a decarboxylation reaction as the primary photochemical step. Confirmation of the participation of free radical intermediates came from the initiation of the free radical polymerization of acrylamide with rates as shown in Table 2.1. 

Spin-traps DMPO (5,5-dimethyl-l- pyrroline-N-oxide), MNP (2-methyl-2-nitroso-propane, dimer), dG (2 -deoxyguanosine monophosphate), 8-HOdG standard (8-hydroxy-2 -deoxyguanosine) and deferoxamine mesylate were purchased from Sigma phosphate buffer (pH 7.4), hydrogen peroxide (H2O2) (30%), were purchased from Merck. All other chemicals used were of analytical quality. 

Thermal decomp, of DTBPO Spin trap, using 2-methyl-2-nitroso propane... 

The thermal cis-trans isomerizations of nitrosomethane and 2-methyl-l-nitroso-propane obey first order kinetics with activation energies (kcal.mole ) and log y4(sec ) of 19.1 and 22.1, and 11.6 and 13.9, respectively . Both direct and indirect isomerization mechanisms were considered, viz. 

Deuterium isotope effects in the reactions of 2-nitroso-2-methyl propane with formaldehyde, glyoxylate, glyoxylic acid, pyruvic and phenylglyoxylic acid... 

Morpholin 4-Chlor- XI/2, 696 Propan 2-Chlor-2-methyl-l-nitroso-X/l, 937, 943 f. 

Propan ( + )-l-Cyclohexyl-2-nitroso-E16a, 968 (NH2 - NO) Propanal 2-Piperidino-2-methyl- E3, 584 (En-Amin +... 

Propan 2-Methyl-2-nitroso-l-phenyl-E16a. 970 (NH-OH NO) Propansaure... 

Propan 2-(Acetoxy-methyl)-l,3-diacetoxy-2-nitroso- (dimer) X/l, 966... 

Propan l-(2-Methoxy-5-methyl-phenyl)-2-nitro-l-nitroso-(dimer) X/l, 74 Propansaure 2-Amino-3-(4-hydroxy-phenyl)- -(carboxy-methylamid) XV/2, 195, 617 3H-Pyrazol 3-Cyclopropyl-4,5-dimethoxycarbonyl-3-methyl-E14, 994 (R2C = N2 4- In) Pyrimidin 2,6-Dimethoxy-5-(2-methoxycarbonyl-ethenyl)-4-methyl- E9b/2, 224f. 

Phenol 3-(bzw. 4)-Methyl-2-pyrrolidino- VI/lc, 910 Piperidin l-[2(bzw. 4)-Hydroxy-phenyl]- E16d, 656 [Dialkylami-nierung (Minisci-Reaktion)] Propan m . .ro-l-(3,4-Dimethyl-phenyl)-2-nitroso- E16a, 968 (NH2 - NO)... 

Propanal, 3-(nitrosomethylamino)-CH5-N(NO)-(CHj)2-CHO 1-Propanamine,A/,2-dirTiethyl-A/-nitfoso-CH5CH(CHj)CHrN(NO)-CH, 1-Propanamine, W-ethyl-2-methyl-W-nitroso-CH3CH(CHj)CHrN(NO)-CHzCHj 1-Propanamine, A/-ethyl-A/-nitroso-CH,CH3CHrN(NO)-CH CH,... 

Trapping free radicals by the spin trapping technique. This technique is used for the detection and identification of short-lived free radicals by detecting the ESR spectra of nitroxyl addition products (spin adducts) of free radicals (R ) to nitroso (e.g. 2-nitroso-2-methyl propane, t-butyl nitroxide 10.19), nitrobenzene (10.20), pentamethylnitrobenzene (10.21)) and nitrone (phenyl-N-tert-butyl nitrone) (10.22) compounds called spin traps ... 

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