75376-75-9Relevant academic research and scientific papers
Radical-nucleophilic substitution (SRN1) reactions. Part 7. Reactions of aliphatic α-substituted nitro compounds
Al-Khalil,Bowman,Gaitonde,Marley,Richardson
, p. 1557 - 1565 (2007/10/03)
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.
REACTIONS OF THIOLATE ANIONS WITH 2-SUBSTITUTED-2-NITROPROPANES
Bowman, W. Russel,Richardson, Geoffrey D.
, p. 1551 - 1554 (2007/10/02)
Thiolates undergo substitution reactions with 2-substituted-2-nitropropanes by an SRN1 mechanism or are oxidised to disulphides by an ionic mechanism.
Radical-Nucleophilic Substitution (SRN1) Reactions: Preparation and Reactions of α-Nitrosulphides
Bowman, W. Russell,Richardson, Geoffrey D.
, p. 1407 - 1413 (2007/10/02)
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.
