21272-84-4

Upstream product

• 873-55-2 sodium benzenesulfonate 
• 108-03-2 1-Nitropropane 
• 74737-89-6 phenylsulfonylnitromethane sodium salt 
• 107-08-4 1-iodo-propane 
• 21272-85-5 phenylsulfonylnitromethane 
• 75-03-6 ethyl iodide 

Downstream Products

• 1620141-55-0 (R)-naphthalen-1-yl 4-nitro-4-(phenylsulfonyl)hexanoate 

Relevant academic research and scientific papers

Enantioselective synthesis of α-nitro-δ-ketosulfones via a quinine-squaramide catalyzed conjugate addition of α-nitrosulfones to enones

Conjugate addition of α-nitrosulfones to vinyl ketones in the presence of 0.2 mol% of a quinine-squaramide organocatalyst afforded α-nitro-δ-ketosulfones possessing a tetrasubstituted chiral center in excellent yield and enantioselectivity in most cases. This strategy also offers a facile and convenient entry into γ-sulfonylhydroxamates that are one carbon homologs of potent enzyme inhibitors.

Electrooxidative coupling of salts of nitro compounds with halide, nitrite, cyanide, and phenylsulfinate anions

Electrolysis of salts of primary and secondary nitro compounds (nitroethane, 1- and 2-nitropropanes, nitrocyclohexane, and nitrocycloheptane) in the presence of excess halide, nitrite, cyanide, and phenylsulfinate anions under undivided and divided amperostatic electrolysis conditions in a two-phase medium (CH2Cl2/H2O) produces geminal nitrohalides (35-85% yields), dinitro compounds (15-51%), nitronitriles (6-27%), and nitrosulfones (50-70%). The salts of secondary nitro compounds form the products of oxidative coupling with halide and phenylsulfinate anions under the undivided electrolysis conditions. In all other cases, divided electrolysis is required.

Oxidative Substitution of Nitroparaffin Salts

α,α-Dinitro compounds, α-nitro sulfones, and α-nitro nitriles are obtained in excellent yields when nitroparaffin salts are coupled to nitrite, benzenesulfinate, and cyanide ions by the agency of potassium ferricyanide.

A NEW METHOD FOR THE SYNTHESIS OF SECONDARY α-NITRO SULPHONES

Nitro(phenylsulphonyl)methane was preferentially C-alkylated by different alkyl halides using the PTC technique to produce secondary α-nitro sulphones (2-9) in good yield (65-75percent).