553-97-9Relevant articles and documents
Emitters of chemiluminescence occurring during autoxidation of substituted hydroquinones in water
Kalinichenko,Kalinichenko,Odaryuk,Kanibolotskaya,Shendrik
, p. 1476 - 1480 (2017)
A mathematical processing method for determination of spectral parameters of chemiluminescence emitters during the autoxidation of phenolic compounds in aqueous-alkaline media has been developed. The presence of a single luminescence emitter (the corresponding p-benzoquinone in the triplet state) has been demonstrated in the hydroquinone–oxygen–water system. The emitters spectra have been obtained.
Can Donor Ligands Make Pd(OAc)2a Stronger Oxidant? Access to Elusive Palladium(II) Reduction Potentials and Effects of Ancillary Ligands via Palladium(II)/Hydroquinone Redox Equilibria
Bruns, David L.,Musaev, Djamaladdin G.,Stahl, Shannon S.
supporting information, p. 19678 - 19688 (2020/12/18)
Palladium(II)-catalyzed oxidation reactions represent an important class of methods for selective modification and functionalization of organic molecules. This field has benefitted greatly from the discovery of ancillary ligands that expand the scope, reactivity, and selectivity in these reactions; however, ancillary ligands also commonly poison these reactions. The different influences of ligands in these reactions remain poorly understood. For example, over the 60-year history of this field, the PdII/0 redox potentials for catalytically relevant Pd complexes have never been determined. Here, we report the unexpected discovery of (L)PdII(OAc)2-mediated oxidation of hydroquinones, the microscopic reverse of quinone-mediated oxidation of Pd0 commonly employed in PdII-catalyzed oxidation reactions. Analysis of redox equilibria arising from the reaction of (L)Pd(OAc)2 and hydroquinones (L = bathocuproine, 4,5-diazafluoren-9-one), generating reduced (L)Pd species and benzoquinones, provides the basis for determination of (L)PdII(OAc)2 reduction potentials. Experimental results are complemented by density functional theory calculations to show how a series of nitrogen-based ligands modulate the (L)PdII(OAc)2 reduction potential, thereby tuning the ability of PdII to serve as an effective oxidant of organic molecules in catalytic reactions.
Activated Carbon-Promoted Dehydrogenation of Hydroquinones to Benzoquinones, Naphthoquinones, and Anthraquinones under Molecular Oxygen Atmosphere
Kim, Sanghun,Matsubara, Ryosuke,Hayashi, Masahiko
, p. 2997 - 3003 (2019/03/08)
We found that the activated carbon-molecular oxygen system promotes the conversion of hydroquinones to benzoquinones, naphthoquinones, and anthraquinones, which are often found in natural products and pharmaceuticals. In particular, the one-pot synthesis of naphthoquinones and anthraquinones involving a Diels-Alder reaction is a useful protocol for this purpose.