Nitric esters addition compounds

Certain nitric esters are capable of forming addition products with aromatic nitro compounds (see pp. 167, 169), as indicated by T. Urbanski [65]. 

Because of the known vasodilating activity of isohexide nitric esters, several attempts were made to improve or modify these compounds by introducing additional substituents at the second hydroxyl group. On the one hand, this type of molecular modification would influence the polarity and... 

As shown by T. Urbanski [143] between 1933 and 1937, there is a group of molecular addition compounds whose existence cannot be explained by all the points mentioned above. They are addition compounds of certain nitro compounds with esters of nitric acid. Thus many aromatic mononitro compounds form addition compounds with mannitol hexanitrate, and some aromatic trinitro compounds do so with erythritol tetranitrate (Vol. II). On the basis of these facts the author suggests that two main reasons are responsible for the formation of these addition compounds ... 

The polarity of nitric ester. All esters forming addition compounds possess high polarity. On the contrary, the ester of low polarity-penthaerythritol tetranitrate does not give addition compounds with any of the above mentioned aromatic nitro derivatives. 

The unsaturated character of these trialkyl esters was shown by the ease with which they were attacked by nitric acid, but still more clearly by the formation, with evolution of heat, of stable crystalline addition compounds when they were mixed with cuprous halides. Thus CuC1.P(OC2H5)3 was described as consisting of colourless crystals melting at 190° to 192° C. and soluble in organic solvents.4 This property they share with phosphine, alkylphosphines and phosphorus trihalides. The phosphoric esters were quite indifferent to cuprous halides. Nor were such addition compounds formed either by phosphorous acid itself or by the dialkyl esters, which may show that the latter compounds have the unsymmetrical formula. Phosphorous acid probably exists in both forms, but first as P(OH)3, i.e. when produced from PC13 and Ha0.5 This may be transformed into the unsym-metrieal form through an addition compound HC1.P(0H)3,4 and probably also exists in the form of complex molecules, such as... 

As mentioned earlier, when NO concentration exceeds that of superoxide, nitric oxide mostly exhibits an inhibitory effect on lipid peroxidation, reacting with lipid peroxyl radicals. These reactions are now well studied [42-44]. The simplest suggestion could be the participation of NO in termination reaction with peroxyl radicals. However, it was found that NO reacts with at least two radicals during inhibition of lipid peroxidation [50]. On these grounds it was proposed that LOONO, a product of the NO recombination with peroxyl radical LOO is rapidly decomposed to LO and N02 and the second NO reacts with LO to form nitroso ester of fatty acid (Reaction (7), Figure 25.1). Alkoxyl radical LO may be transformed into a nitro epoxy compound after rearrangement (Reaction (8)). In addition, LOONO may be hydrolyzed to form fatty acid hydroperoxide (Reaction (6)). Various nitrated lipids can also be formed in the reactions of peroxynitrite and other NO metabolites. 

Cellulose dissolves in Schweitzer s reagent, an ammoniacal solution of cupric oxide. After treatment with an alkali, ibe addition of carbon disulfide causes formation of sodium xanihate. a process used in the production of rayon. Sec also Fibers. The action of acetic anhydride in the presence of sulfuric acid produces cellulose acetates, the basis for a line of synthetic materials. See also Cellulose Ester Plastics (Organic). Nitrocelluloses are produced hy ihc action of nitric acid and sulfuric acid on cellulose, yielding compounds that are highly flammable and explosive. See also Explosives. 

In the methyl ester fraction of the spent acid from the nitric acid reaction (Figure 10), the methyl ether esters of p-hydroxybenzoic, vanillic, and syringic acids and the methyl esters of benzoic acid and the di- and tricarboxybenzenes have been found. These compounds are also present in the chromatogram of the basic extract, as are the methyl esters of the tetracarboxybenzenes and mellitic acid. In addition, dehydrodivanillic acid or pentacarboxybenzene or both are present in both chromatograms... 

In addition, m-cresol is used to produce plant protection agents such as feni-trothion. The manufacturing process involves nitrosation of m-cresol with nitrous acid esters in isopropanol, and subsequent oxidation of the nitroso compounds with nitric acid to yield 4-nitro m-cresol (or its sodium salt), which, when acted upon by 0,0-dimethyl thiophosphoric acid chloride, gives fenitrothion. 

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