122983-47-5Relevant articles and documents
Metal-free reduction of unsaturated carbonyls, quinones, and pyridinium salts with tetrahydroxydiboron/water
Li, Tiejun,Peng, Henian,Tang, Wenjun,Tian, Duanshuai,Xu, Guangqing,Yang, He
, p. 4327 - 4337 (2021/05/31)
A series of unsaturated carbonyls, quinones, and pyridinium salts have been effectively reduced to the corresponding saturated carbonyls, dihydroxybenzenes, and hydropyridines in moderate to high yields with tetrahydroxydiboron/water as a mild, convenient, and metal-free reduction system. Deuterium-labeling experiments have revealed this protocol to be an exclusive transfer hydrogenation process from water. This journal is
1-Methyl-1,4-cyclohexadiene as a Traceless Reducing Agent for the Synthesis of Catechols and Hydroquinones
Baschieri, Andrea,Amorati, Riccardo,Valgimigli, Luca,Sambri, Letizia
, p. 13655 - 13664 (2019/10/28)
Pro-aromatic and volatile 1-methyl-1,4-cyclohexadiene (MeCHD) was used for the first time as a valid H-atom source in an innovative method to reduce ortho or para quinones to obtain the corresponding catechols and hydroquinones in good to excellent yields. Notably, the excess of MeCHD and the toluene formed as the oxidation product can be easily removed by evaporation. In some cases, trifluoroacetic acid as a catalyst was added to obtain the desired products. The reaction proceeds in air and under mild conditions, without metal catalysts and sulfur derivatives, resulting in an excellent and competitive method to reduce quinones. The mechanism is attributed to a radical reaction triggered by a hydrogen atom transfer from MeCHD to quinones, or, in the presence of trifluoroacetic acid, to a hydride transfer process.
Finding a new pathway for acid-induced nitrite reduction reaction: Formation of nitric oxide with hydrogen peroxide
Puthiyaveetil Yoosaf, Mohammed Ajmal,Ghosh, Somnath,Narayan, Yatheesh,Yadav, Munendra,Sahoo, Subash Chandra,Kumar, Pankaj
supporting information, p. 13916 - 13920 (2019/10/02)
Here, we report a new pathway for nitrite reduction chemistry, formation of cobalt-nitrosyl ({CoII-NO}8) with H2O2 in the reaction of a CoII-nitrito complex with a one-fold acid (H+) via the formation of a CoII-nitrous acid intermediate ({CoII-ONOH}). Mechanistic investigations using 15N-labeled-15NO2- revealed that the N-atom in the {CoII-NO}8 complex is derived from the nitrito ligand, and H2O2 came from the homolysis of the ON-OH moiety. Spectral evidence supporting the formation of the CoII-ONOH intermediate and the generation of H2O2 is also presented.
