Nitrosobenzene dimethylaniline

In contradistinction to nitrosobenzene these bases, and p-nitroso-dimethylaniline also, exist only in the unimolecular green form. 

Some IP data have been published for -substituted nitrosobenzenes with substituents like Me, Cl, NMe2 and OMe128. Four IP(n ) values between 7.78 (4-nilroso-iV,iV-dimethylaniline, 65) and 9.02 eV (4-chloronitrosobenzene, 66) were observed. The corresponding value of l-methyl-3-nitroso-2-phenylindole (67) was found to be 7.50 eV130. 

Lraole sec for the oxidation by peroxomonosulphate at 30 °C in 47% ethanol-water solvent. From a comparison of the rate coefficient with that observed for the oxidation of nitrosobenzene by peroxoacetic and peroxochlor-acetic acids, they concluded that the mechanism is similar to that described above for the oxidation of N,N-dimethylanilines. 

Nitrosobenzene, CjHsNO, which is obtained by the oxidation of phenylhydroxylamine, and p>nitrosodimethylaniline, p-(CH3)2NCjH4NO, which is easily prepared by the nitrosation of dimethylaniline, are fairly specific oxidizing agents for the preparation of aromatic aldehydes from benzyl halides or tosylates and of a-dicarbonyl compounds from from a-halo ketones [984, 985]. Also, a methylene group flanked by two carbonyls can be oxidized to a carbonyl group by nitrosodimethylaniline [986]. Pyridine is frequently used to form quaternary pyridinium salts from reactive halides prior to their oxidation to aromatic aldehydes, a-ketoaldehydes, or a-diketones [984] (equations 22 and 23). 

A broad range of aromatic and aliphatic amines are readily oxidized to their corresponding A-oxides using the MTO/H2O2 catalytic system. The oxidation of aryl amines proceeds ca. 50 times faster than without catalyst [3, 18]. Nitrosobenzene is obtained by the oxidation of aniline (eq. (6)) while the oxidation of 4-substi-tuted A,A-dimethylanilines yields the A-oxide as the only product. It has been found that electron-withdrawing substituents present on the substrate inhibit the reaction. 

Synonyms Accelerine Aniline, N,N-dimethyl-4-nitro- Aniline, N,N-dimethyl-p-nitroso- Benzenamine, N,N-dimethyl-4-nitroso- 4-(Dimethylamino) nitrosobenzene p-(Dimethylamino) nitrosobenzene N,N-Dimethyl-4-nitrosoaniline N,N-Dimethyl-4-nitrosobenzenamine Dimethyl (p-nitrosophenyl) amine NDMA Nitrosoaniline, N,N-dimethyl-p- 4-Nitrosodimethylaniline 4-Nitroso-N,N-dimethylaniline p-Nitrosodimethylaniline p-Nitroso-N,N-dimethylaniline Paranitrosodimethylanilide Ultra brilliant blue P... 

---