Alkanes nitroalkane

Nitroparaffias (or nitroaLkanes) are derivatives of the alkanes ia which one hydrogen or more is replaced by the electronegative nitro group, which is attached to carbon through nitrogen. The nitroparaffins are isomeric with alkyl nitrites, RONO, which are esters of nitrous acid. The nitro group ia a nitroparaffin has been shown to be symmetrical about the R—N bond axis, and may be represented as a resonance hybrid ... 

Scheme 7.5. BusSnH-catalyzed reduction of nitroalkanes to alkanes...

Smith, R. M. and Finn, N., Comparison of retention index scales based on alkyl aryl ketones, alkan-2-ones and 1-nitroalkanes for polar drugs on re-versed-phase high-performance liquid chromatography,. Chromatogr., 537, 51,1991. 

Gem-nitro imidazolyl alkanes undergo Sjy l reactions with the anion of various nitroalkanes, as shown in Eq. 5.36.54 The nitro group is replaced by hydrogen in 80-90% yield on treatment with Bu3SnH (see Chapter 7, which discusses radical denitration). 

Table 7.2. Bu3SnH-catalyzed reduction of nitroalkane to alkanes...

The nitration of moderate to high molecular weight alkane substrates results in very complex product mixtures. Consequently, these reactions are only of industrial importance if the mixture of nitroalkane products is separable by distillation. Polynitroalkanes can be observed from the nitration of moderate to high molecular weight alkane substrates with nitrogen dioxide. The nitration of aliphatic hydrocarbons has been the subject of several reviews. 

Olah showed that nitrations can be split into the three categories of electrophilic, nucleophilic and free radical nitration. Free radical nitrations are extensively used for the industrial synthesis of low molecular weight nitroalkanes from aliphatic hydrocarbons. Nucleophilic nitration is the basis for a number of important methods for the synthesis of nitro and polynitro alkanes. Generally speaking only electrophilic nitration is of preparative importance for the... 

Tertiare Nitroalkane werden mit Jod-trimethyl-silan in Dichlor- oder Trichlor-methan in ausgezeichneten Ausbeuten in Jod-alkane fiberfuhrt1 ... 

I-Nitroalkenes. Anions of nitroalkanes react with benzeneselenenyl bromide in THF to form nitro(phenylseleno)alkanes, which usually are not isolated but rather are converted directly into nilroalkenes by oxidation with 35% aqueous H202 (equation I).1... 

Alkalsit is a Ger blasting expi which is described in PATR 2510(1958), p Ger 3 Alkanes, Nitrated Derivatives (Nitrated Aliphatic Hydrocarbons). The first nitro-alkane described in the literature was 1,2-dinitroethane, prepd in Russia by A.Semenov. Since then hundreds of nitroalkanes, some of them explosive, were obtained. The reference given below describes old and new methods of prepn of nitro alkanes. Most of expl nitro alkanes are described in this dictionary under their parent names, such as methane, ethane, propane, etc Ref 0. vonSchickh, AngewChem 62, 547-56 (1950)(Chemie und Technologie der Nitro-alkane)... 

Method of Wakita, Yoshlmoto, Miyamoto, and Watanabe The Wakita et al. method [46] has been derived with a set of 307 liquid compounds, including alkanes, alkenes, alkynes, halogenated alkanes, alkanols, oxoalkanes, alkanones, alkyl alkanoates, alkanethiols, alkanenitriles, nitroalkanes, and substituted benzenes, naphthalenes, and biphenyles. The model equation is... 

In extension, some retention index scales were proposed to mimic the Kovats index in GC. Alkanes, n-alkylbenzenes, alkan-2ones, alkylary] ketones, nitroalkanes, or polynuclear aromatic hydrocarbons were the advocated solutes. None of these scales is reliable, and observed indexes are not stable with variation in eluent composition, which precludes their use as a Kovats scale. 

The C — H bonds in alkanes are broken to form nitroalkanes with nitric acid at 400°C or more. 

Deoxygenation of sulfoxides, selenoxides, and nitro alkanes. P2L, is a useful reagent for deoxygenation of sulfoxides, selenoxides, and primary nitroalkanes to sulfides, selenides, and nitriles, respectively. The reactions occur in less than 2 hours at2r. 

---