Nitro aliphatic

Some nitro-compounds are themselves coloured and can be used as dyestuffs, e.g. picric acid. In this case the nitro-group can be considered to be the chromophore. For aliphatic nitro-compounds see nitroparaffins. 

Aliphatic nitro compounds. These are isomeric with the alkyl nitrites and may be prepared from the alkyl halide and silver nitrite, for example C,H,aBr + AgNOj — C Hj NO + AgBr... 

For a discussion of the Reactions and Characterisation of Aliphatic Nitro Compounds, see Section IV,16B.)... 

The following reactions will assist in the detection of aliphatic nitro compounds. 

Most aliphatic nitro compounds are liquids the physical properties (boiling point, density and refractive index) therefore provide valuable information for purposes of identification. 

The physical properties of a number of aliphatic nitro compounds are listed in Table IV,16B. 

Neta.1 Ama.lga.ms. Alkali metal amalgams function in a manner similar to a mercury cathode in an electrochemical reaction (63). However, it is more difficult to control the reducing power of an amalgam. In the reduction of nitro compounds with an NH4(Hg) amalgam, a variety of products are possible. Aliphatic nitro compounds are reduced to the hydroxylamines, whereas aromatic nitro compounds can give amino, hydra2o, a2o, or a2oxy compounds. 

Thiophenealdehydes have been condensed with aliphatic aldehydes, methyl ketones,cyclic ketones, " benzyl cyanides,and aliphatic nitro compounds to the corresponding vinylthiophenes. By the use of potassium methylate, 2-thiophenealdehyde has been condensed with the reactive methyl groups of iV-heterocyclic compounds. Thiophenealdehydes have... 

Reaction of an Aminopyridine with an Aliphatic Nitro Compound. 289... 

In this method the nitro group in the aliphatic nitro compound is usually present on a carbon atom, which is also activated by CO-functioiiality (aldehyde, ester, arylketoiie). A successful application of this method is the Borsche modification of the Friedlander synthesis, involving condensation of A-(3-amino-4-picolylidene)-p-toluidine (17) with [Pg.289]

Reactions of aliphatic nitro alcohols with heterocycles 98UK39. 

A similar reaction pathway is even described for an aliphatic nitro group nucleophilic displacement. Nitrohydrazones 126 with sodium hydride provide acceptable yields (40-60%) of tricyclic [l,2,4]triazolo[5,l-c][l,4]benzoxazines 128... 

S909). First, an addition of the cyano group takes place to give intermediate 127, in which nucleophilic substitution of aliphatic nitro group provides the final product 128 (Scheme 20). 

Electrochemically generated nickel is very selective for the reduction of ai compounds into anilines, in which alkenyl, alkyhyl, halo, cytino, formyl, ind benzyloxy groups are not affected. Sodium snlfide has been used for the selective reduction of at group in the presence of aliphatic nitro groups (Tq. 6.44. ... 

A reagent of nickel boridei/hydiazine hydrate reduces both aromadc and aliphatic nitro compotmds. For example, it has been used for synthesis ofd-fbenzyloxyiindole and -alkyltryp-... 

Nitro-bakterien, n.pl. nitrobacteria, -benzol, -benzin, n. nitrobenzene, -chinon, n. nitro-quinone. -cocussaure, /. nitrocoeeic acid, -derivat, n. nitro derivative, -farbstoff, m. nitro dye. -fettkorper, m. aliphatic nitro compound, -fettsaure, /. nitro fatty acid, -gruppe, /. nitro group, -halogenbenzole,... 

Aromatic nitro compounds are hydrogenated very easily aliphatic nitro compounds considerably more slowly. Hydrogenations have been carried out successfully under a wide range of conditions including vapor phase (S9). Usually the goal of reduction is the amine, but at times the reduction is arrested at the intermediate hydroxylamine or oxime stage nitroso compounds never accumulate, although their transient presence may appreciably influence the course of reaction. In practice, nitro compounds often contain other reducible functions that are to be either maintained or reduced as well. 

Hydrogenation of aromatic nitro compounds is very fast, and the rate is limited often by the rate of hydrogen transfer to the catalyst. It is accordingly easy to use inadvertently more catalyst than is actually necessary. Aliphatic nitro compounds are reduced much more slowly than are aromatic, and higher catalyst loadings (6,11) or relatively lengthy reduction times may be... 

Solubility. No quant data is in the literature. In Ref 11, p 19 die order of decreasing soly is given as w, ketones, ales)) esters) organic acids, aliphatic nitro compds) ethers, chlorinated hydrocarbons, hydrocarbons. Within each class the solubility decreases with increasing chain length... 

Gilliland H.B. Hass, Synthesis of Certain Aliphatic Nitro Compounds" in ADL Synthesis and Testing of High Explosives , Report C-57625, Contr W-19-020-ORD-6436, 3 Jan 1949 (AD-222018), p i 05 21) N.D. Mason,... 

H.B. Hass, The Synthesis of Certain Aliphatic Nitro Compounds , OSRD 1 54 (18 Oct... 

PA. Rifle bullet impact in welded cans gave 4/4 high order detonations. Thermal stability at 135°, acid in 15—30 minutes at 82.2° heat test, 10 minutes at 82.2°. This material and its homologs from other aliphatic nitro compounds and aldehydes have been suggested as substitutes for NG... 

Bowman and Symons145 probed the stability of a series of radical anions involved in the SRN1 substitution for a-substituted aliphatic nitro-compounds [Me2C(X)N02] by studying with ESR at 77 K the succession of events following electron capture by Me2C(X)N02. The radical anions were more concentrated in an ether matrix than in an... 

Aliphatic Nitro Compounds Are in Equilibrium With Aci Forms. 

Nitro Anions Remov of a proton from an aliphatic nitro compound gives a carbanion (R2C-NO2) that can be alkylated at oxygen or carbon. ... 

So do anhydrides and many compounds that enolize easily (e.g., malonic ester and aliphatic nitro compounds). The mechanism is usually regarded as proceeding through the enol as in 12-4. If chlorosulfuric acid (CISO2OH) is used as a catalyst, carboxylic acids can be ot-iodinated, as well as chlorinated or brominated. N-Bromosuccinimide in a mixture of sulfuric acid-trifluoroacetic acid can mono-brominate simple carboxylic acids. ... 

Primary or secondary aliphatic nitro compounds can be hydrolyzed, respectively, to aldehydes or ketones, by treatment of their conjugate bases with sulfuric acid. This is called the Nef reaction Tertiary aliphatic nitro compounds do not give the reaction because they cannot be converted to their conjugate bases. Like 16-2, this reaction involves hydrolysis of a C=N double bond. A possible mechanism is" ... 

When aliphatic nitro compounds are used instead of aldehydes or ketones, no reduction occurs, and the reaction is essentially a Knoevenagel reaction, though it is usually also called a Tollens reaction ... 

Primary and secondary aliphatic nitro compounds have been oxidized to aldehydes and ketones, respectively (RR CHN02 RR C=0) with sodium chlorite under phase-transfer conditions, TPAP, Oxone , as well as with other reagents. 

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