63489-72-5Relevant academic research and scientific papers
Conformational interactions between a phenyl ring and a side-chain halide substituent: a 1H NMR and molecular mechanics study of some 2-aryl-1-halopropanes
Cook, Michael J.,Howe, Trevor J.
, p. 957 - 965 (2007/10/02)
1H NMR data are reported for a series of 2-aryl-1-halopropanes.Vicinal coupling constants in the CH2-CH-fragment show that the rotamer populations about the C-C bond are sensitive to para substituents.The ratio of anti-gauche aryl/halide conformers is greatest when the para substituent is the electron-donating ethyl group and least when it is the strongly electron-withdrawing nitro group.This points to a non-steric conformational interaction involving the ring and the sidechain heteroatom.Comparison of the empirical results with conformational preferences predictedfrom molecular mechanics calculations using the COSMIC force field suggests that the interaction serves to enhance the population of the anti arrangement.
Electrogenerated Base (EG Base) Induced Hydroxymethylation of the Side Chain of Nitroalkylbenzenes with Paraformaldehyde
Torii, Sigeru,Murakami, Yasuo,Tanaka, Hideo,Okamoto, Koichi
, p. 3143 - 3147 (2007/10/02)
Hydroxymethylation of nitroalkylbenzenes with paraformaldehyde was accomplished by electrolysis in a (CH2O)n-DMF-Et4NOTs-(Pt electrode) system.The reaction was found to be catalytic (0.25 faraday/mol) and dependent on the electroreduction of formaldehyde and/or nitroalkylbenzene.A variety of nitroalkylbenzenes were transformed to their corresponding mono- and/or bishydroxymethylated derivatives in good yield.The product yield and selectivity were shown to depend on the order of reagent addition, solvent, supporting electrolyte, and structure of the starting nitroalkylbenzenes.A plausible mechanism of the generation of base catalysts (EG base) in electroreductive media is discussed.
