An-Najah National University

Suleiman Ibrahim Al-Khalil

Biomedical Scienctist,FIBMS,CCHEM MRSC,

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  • Monday, January 1, 2001
  • Radical-nucleophilic substitution (SRN1) reactions. Part 7. Reactions of aliphatic -substituted nitro compounds
  • Published at:J. Chem. Soc., Perkin Trans. 2, 2001, 1557 - 1565, DOI: 10.1039/b103350f
  • -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 -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–NN] 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.

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Suleiman Ibrahim Al-Khalil
Biomedical Scientist,
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