1636-28-8

Upstream product

• 5447-97-2 2-bromo-2-nitropropane 
• 141-52-6 sodium ethanolate 
• 1122-60-7 1-nitrocyclohexane 
• 4028-15-3 1,1-dinitrocyclohexane 
• 3958-63-2 lithium 2-nitropropane 
• 20846-00-8 2-nitro-propan-2-ide 
• 74974-48-4 1-nitro-1-thiocyanatocyclohexane 
• 66463-89-6 1-methyl-1-nitroethyl p-nitrophenyl sulphide 
• 24163-39-1 sodium 2-nitropropane 
• 85632-90-2 1-azido-1-nitrocyclohexane 
• 75376-74-8 1-methyl-1-nitroethyl 1,3-benzothiazol-2-yl sulphide 
• 12349-47-2 cyclohexanenitronate anion 

Downstream Products

• 5749-72-4 isopropylidenecyclohexane 

Relevant academic research and scientific papers

RADICAL-NUCLEOPHILIC SUBSTITUTION (SRN1) REACTIONS: PREPARATION AND REACTIONS OF ALIPHATIC α-NITRO-AZIDES

α-Nitro-azides were prepared by two routes involving intermediate radical-anions, and undergo substitution by an SRN1 mechanism with azides, sulphinates, and thiolates to give loss of nitrite, and with nitronates to give loss of azide.

Radical-nucleophilic substitution (SRN1) reactions. Part 7. Reactions of aliphatic α-substituted nitro compounds

α-Nitrothiocyanates R2C(SCN)NO2 have been prepared by oxidative addition of thiocyanate anion to nitronate anions and undergo SRN1 substitution reactions by loss of thiocyanate with nitronate anions, phenylsulfinate, azide and p-nitro- and p-chloro-benzenethiolates in dipolar aprotic solvents. 2-Nitro-2-thiocyanatopropane and other 2-substituted-2-nitropropanes [Me2C(X)NO2 with X = I, Br, Cl, NO2, PhSO2] react with thiolates by SRN1 reactions and/or redox reactions to give disulfides by a polar abstraction or chain SET (SET2) mechanisms. The products are dependent on the nucleophilicity of the thiolates, the polarisability of the α-substituent, the solvent and the presence of light catalysis, radical traps or strong electron acceptors. 2-Substituted-2-nitropropanes [Me2C(X)NO2 with X = N3, NO2, CN, p-NO2-C6H4-N=N] undergo SRN1 substitutions with thiolates by loss of nitrite. 2-Substituted-2-nitropropanes Me2C(X)NO2 and thiolates only yield disulfides in methanol due to solvation of the nitro groups.

Radical-Nucleophilic (SRN1) Reactions. Part 4. Preparation, Reactions, and Electron Spin Resonance Studies of α-Nitro Azides

2-Azido-2-nitropropane and 1-azido-1-nitrocyclohexane have been prepared by syntheses involving intermediate radical-anions (SRN1 and oxidative addition).SRN1 Reactions between α-nitroazides and azide, benzenesulphinate, and p-chlorobenzenethiolate proceed with loss of nitrite.The SRN1 reaction between 1-azido-1-nitrocyclohexane and the anion of 2-nitropropane proceeds with loss of azide.Reactions between 2-azido-2-nitropropane and the anions of 2-nitropropane and diethyl ethylmalonate yield oxidative dimerisation.E.s.r. spectroscopy has been used to observe electron-capture by 2-azido-2-nitropropane and its dissociation to nitrite and an ill-defined radical which may be (Me2CN3)..The addition of benzenesulphinate and the anion of 2-nitropropane to Me2C.NO2, formed by a minor dissociation route from 2C(N3)NO2>-., has been observed by e.s.r. spectroscopy.

RADICAL-NUCLEOPHILIC SUBSTITUTION (SRN1) REACTIONS OF α-NITRO-THIOCYANATES

α-Nitro-thiocyanates undergo substitution by a SRN1 mechanism with a range of anions to give loss of thiocyanate, corroborating behaviour observed for the intermediate α-nitro-thiocyanato radical-anions by e.s.r. spectroscopy.

Radical-Nucleophilic Substitution (SRN1) Reactions: Preparation and Reactions of α-Nitrosulphides

α-Nitrosulphides were prepared by SRN1 reaction of 2-bromo-2-nitropropane with thiolate anions, and by SN2 attack of sodium 2-nitropropan-2-ide on symmetrical disulphides.The α-nitrosulphides undergo radical-nucleophilic substitution (SRN1) by nitronate, sulphinate, and malonate anions, but not by thiolate anions.