58518-80-2Relevant academic research and scientific papers
Convenient Electrocatalytic Synthesis of Azobenzenes from Nitroaromatic Derivatives Using SmI2
Zhang, Yu-Feng,Mellah, Mohamed
, p. 8480 - 8486 (2017/12/08)
The synthesis of azobenzenes has been a long-standing challenge. Their current preparation at a preparative or industrial scale requires stoichiometric amounts of environmentally unfriendly reactants. Herein, we demonstrate that the catalytic use of electrogenerated samarium diiodide (SmI2) could promote, in one-step synthesis, the reduction of nitrobenzenes into azobenzenes in high yields under mild reaction conditions. This catalytic procedure contains many elements satisfying a sustainable chemical process for the preparation of one of the most widely wanted family of chemical compounds. The easy synthetic procedure, and the absence of precious metals, bases, and nonhazardous substances, already makes our catalytic procedure a serious alternative to currently available methods. This is a promising method for the efficient synthesis of both symmetrical and asymmetrical azo compounds with a high functional group tolerance.
Reaction of arylimodimagnesium with aromatic bifunctional nitriles: Competition and/or cooperation of functional groups affected by electron-accepting ability and location
Okubo, Masao,Sakata, Masayo,Iwatsu, Yuko,Tsurusaki, Nobuyuki,Nakashima, Sawako,Iwamoto, Yoshihito,Nonaka, Harumi,Yamauchi, Akira,Matsuo, Koji
, p. 242 - 252 (2007/10/03)
The reactions of aryliminodimagnesium [ArN(MgBr)2, IDMg] with p′-substituted p-cyanobenzophenones, 1-cyano-9-fluorenone, o-, m- and p-dicyanobenzenes and o-, m- and p-nitrobenzonitriles were examined, and the relative yields of products were referred to the previous results of electron spin resonance studies. The products of condensation with carbonyl and nitro groups and of addition to cyano groups were formed. From the variations of the yields caused by the molar ratio of the magnesium reagent versus substrates and by the substituents of both reactants, the preferred groups were determined. The groups of p- and m-substrates are consistent with the position of highest density of free electrons in the anion radicals, whereas those of the o-substrates are inconsistent The consistency indicates competition of functional groups reflecting the relative ability of single electron acceptance from the reagent, whereas the inconsistency is ascribed to cooperation of neighbouring groups for σ-complexation with the Mg atom of the reagent. The categories of competition and cooperation are discussed in relation to fundamental features and general governing factors proposed for the IDMg reactions of monofunctional substrates.
