5447-97-2Relevant articles and documents
Electrooxidative coupling of salts of nitro compounds with halide, nitrite, cyanide, and phenylsulfinate anions
Ilovaisky,Merkulova,Ogibin,Nikishin
, p. 1585 - 1592 (2007/10/03)
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.
Reactions of 1-Aryl-1,2-dibromo-2-nitropropanes with 2-Nitro-2-propyl Anion in DMSO
Cho, Bong Rae,Suh, Young Sung,Lee, Seung Jae,Cho, Eun Jeong
, p. 3681 - 3682 (2007/10/02)
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Polynitro-Substituted Strained-Ring Compounds. Synthesis, Mechanism of Formation, and Structure of trans-Dinitrocyclopropanes
Wade, Peter A.,Dailey, William P.,Carroll, Patrick J.
, p. 5452 - 5456 (2007/10/02)
1,2-Dinitrocyclopropane, 1,2-dimethyl-1,2-dinitrocyclopropane, and 1,2-diethyl-1,2-dinitrocyclopropane have been prepared in 23-36percent yield by oxidative cyclization of the corresponding open-chain 1,3-dinitronate dianions with iodide in DMSO.In each case only the trans isomer of the dinitrocyclopropane was obtained.Treatment of 2,4-dibromo-2,4-dinitropentane with the lithium salt of 2-nitropropane gave trans-1,2-dimethyl-1,2-dinitrocyclopropane, suggesting the intermediacy of a halonitro nitronate intermediate in the oxidative cyclization process.Further mechanistic studies using m-dinitrobenzene suggest either an internal single-electron transfer, nonchain pathway or an internal SN2 process leading to the dinitrocyclopropanes.An X-ray crystallographic study performed on trans-1,2-dinitrocyclopropane indicates substantially shortened distal C-C bonds (1.47 Angstroem) and bisected conformations for each nitro group.Ab initio calculations using a 4-31G basis set are in agreement with the X-ray data, except longer distal C-C bonds (1.49 Angstroem) are calculated.Ab initio calculations using a variety of basis sets were performed on nitrocyclopropane as a model.