99404-80-5Relevant academic research and scientific papers
Aryliminodimagnesium Reagents. XIX. Effects of Miscellaneous Metal Halides on Oxidative Self-Coupling of the Reagent, and on Its Condensation with Nitrobenzene. A New Preparative Route to o,o'-Dihydroxyazobenzene
Okubo, Masao,Shiku, Haruko
, p. 196 - 201 (2007/10/02)
Fourteen metal halides (MXn) were each added to the solution of aryliminodimagnesium (p-RC6H4N(MgBr)2, IDMg) in tetrahydrofuran, and the effect of MXn on relative yields of products was examined in the following three IDMg reactions: (A) oxidative coupling leading to symmetrical azobenzene, (B) condensation with nitrobenzene, and (C) condensation with o-hydroxy-substituted (o-HO) nitrobenzene.Reaction A was promoted by addition of CuCl2, and the yield of azoxybenzenes in reaction B was improved by addition of NiCl2 or CdCl2.Reaction C was similarly modified by addition of CdCl2 so as to improve the yield of o-HO-azoxybenzenes.Their acetyl derivatives underwent a facile photoinduced migration of azoxy oxygen and were successively hydrolyzed to afford bidentate chelating agents, o,o'-(HO)2-azobenzenes.
Aryliminodimagnesium Reagents. XVI. Formation of o-Hydroxyazoarenes by Condensation with o-Hydroxynitroarenes. Favorable Role of o-Hydroxyl Group in the Reaction
Okubo, Masao,Nakashima, Takanori,Shiku, Haruko
, p. 1621 - 1625 (2007/10/02)
Hydroxy(HO)-azoxy and -azoarenes were formed by condensation of ArN(MgBr)2 with o-, m-, and p-HO-nitrobenzenes; nuclear substitution took place as a minor or a major pathway. o-HO-azobenzene was obtained in sufficiently high yield.Relative yields of the products varied according to the position of HO group and reaction conditions.The yield variation was explained by the effects of relative efficiency of single electron transfer, ?-complexation, and cooperation of reagent molecules.
