39501-58-1Relevant academic research and scientific papers
Reactivity of phenolic nucleophiles towards nitroso compounds. Part 2. Reaction with alkyl nitrites (O-nitroso compounds)
Leis, J. Ramon,Rios, Ana,Rodriguez-Sanchez, Luiza
, p. 2729 - 2734 (2007/10/03)
Second-order rate constants, k, have been measured for the reaction of substituted phenolate ions with alkyl nitrites in aqueous solution at 25 deg C. The final products of this reaction were identified as aromatic C-nitroso compounds and/or NO2-. Nitrosation of the phenolate ion yields ca. 90 percent of the p-nitroso product. However, methylation of the activated position of the ring (as in 4-methylphenol) does not result in the decrease in the overall reaction rate that would be expected. The reactivity of all the phenolate ions studied correlates well with their basicity, with the Hammett ?- constant and with their reactivity in other reactions in which they are known to act as O-nucleophiles. All these facts suggest that the reaction of aryloxide ions with alkyl nitrites always occurs through the oxygen atom to yield an unstable O-nitroso compound. This intermediate is likely to undergo an internal rearrangement of the NO group to give the corresponding C-nitroso product, competing with homolysis of the O-NO bond to yield nitric oxide. Oxidation of NO in the presence of O2 gives N2O3, which could act as a nitrosating agent towards ArO-. Hydrolysis of N2O3 in basic media accounts for the presence of the nitrite ion as one of the products.
A facile access to substituted 2-nitrosophenols and 2-nitrophenols via regioselective nitrosation of resorcinol monoethers
Maleski,Kluge,Sicker
, p. 2327 - 2335 (2007/10/02)
Solid sodium nitrite in anhydrous propionic acid is an effective system for regioselective nitrosation of the subject compounds. High yields of pure 2-nitroso products are obtained rapidly and efficiently. Attack at the 4-position becomes competitive if water is present in the medium. The 5-alkoxy (but not the 3,5-dialkoxy)-2-nitrosphenols can be easily oxidized with nitric acid to yield the corresponding 2-nitro compounds.
NITROSODEALKYLATION AS A SELECTIVE METHOD FOR THE PRODUCTION OF SUBSTITUTED ORTHO- AND PARA- NITROSOPHENOLS
Shpinel', Ya.I.,Klimova, I.V.,Belyaev, E.Yu.
, p. 1309 - 1312 (2007/10/02)
In the reaction of nitrosylsulfuric acid with sterically hindered phenols and 1,3-dialkoxybenzenes the corresponding o- and p-nitrosophenols are formed.In the series of sterically hindered phenols the reaction is ortho-specific, and this is explained by t
