By A. V. Topchiev
Nitration of Hydrocarbons and different natural Compounds tackles quite a few matters within the technique of substituting hydrogen atoms within the fragrant or heterocyclic nucleus, or in saturated hydrocarbon, via nitro teams. The name first covers the nitration of fragrant and heterocyclic compounds with nitric acid and nitrating mix, after which proceeds to discussing the mechanism of the nitration of fragrant compounds with nitric acid and nitrating blend. subsequent, the choice bargains with the nitration of saturated, aromatic-aliphatic and unsaturated hydrocarbons with nitric acid. The textual content additionally talks concerning the nitration with nitrogen oxides, in addition to the nitration of amines. The final bankruptcy information the nitration of natural compounds with natural and inorganic nitrates and nitroxyl. The booklet could be of significant curiosity to scholars, researchers, and practitioners of natural chemistry.
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Extra info for Nitration of Hydrocarbons and Other Organic Compounds
By reducing the product to aminopyridine which was identi fied as jS-aminopyridine F R I E D L proved t h a t the nitration product was ß-nitropyridine. This case served to confirm the rule t h a t the presence of a tertiary nitrogen atom orientates negative substituents first of all to the jS-position. Nitration of 1-hydroxypyridine with a mixture of concentrated sulphuric and concentrated nitric acids at 100°C gives 4-nitro-l-hydroxypyridine Nitration of Aromatic and Heterocyclic Compounds 29 .
This weakening of the ring can occur in two different places (I and II) : 02N (I) H 0 + 0—Hg—ONO2 Hg NO2 0 O2N H 0—Hg—ONO2 ì\ NO2 HO +HNO3 : \ -Ν02+ΗΝθ2+ H g 0 O2N or (Π) 02N 0 Hg 0 H O2N O2N H OH HO \ - N 0 Hg +HNO3 Y \ +HNO2+ Hg NO2 OoN ZAKHAROV'S experiments show that the formation of nitrophenols takes place only when the concentration of nitric acid is low (below 60 per cent), when its oxidizing properties are most in evidence. If nitric acid of relatively high concentration (65-70 per cent) is used, at a temperature of 60-65°C which does not favour its oxidizing action, only nitrobenzene is obtained, at the beginning of the reaction ; nitrophenols appear only some time after the beginning of the process following the lowering of nitric Nitration of Aromatic and Heterocyclic Compounds 51 acid concentration in the reaction mixture.
Mesitylene is distilled off from the aqueous distillate and the nitro-mesitylene is recrystallized from alcohol; it separates out on cooling in the form of prisms . BAMBERGER and R I S I N G  used the following method of nitration to prepare mononitromesitylene : concentrated nitric acid (sp. gr. 1-51; 100 g) is introduced into a mixture of mesitylene (100 g) and glacial acetic acid (400 ml). A vigorous reaction, accompanied by evolution of heat, takes place and the liquid begins to boil; boiling is maintained for 50 min.