52755-34-7Relevant articles and documents
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.
Radical-Nucleophilic Substitution (SRN1) Reactions. Part 2. Preparation and Reactions of α-Nitrosulphides
Bowman, W. Russell,Rakshit, Devajvoti,Valmas, Michael D.
, p. 2327 - 2336 (2007/10/02)
A range of α-nitrosulphides have been prepared by oxidative addition of thiolate anion to the anion of 2-nitropropane, SN2 attack of the anion of 2-nitropropane on symmetrical disulphides, and SRN1 reaction of 2-substituted-2-nitropropanes with thiolate anions.The α-nitrosulphides undergo SRN1 substitution with the anion of 2-nitropropane, and SRN1 substitution or redox reactions with thiolate anions.The electron spin resonance (e.s.r.) spectrum of the radical-anion of 1-methyl-1-nitroethyl pyrimidin-2-yl sulphide has been observed.
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.