59986-60-6Relevant articles and documents
Electrochemical reduction of 3-phenyl-1,2-benzisoxazole 2-oxide on boron-doped diamond
Kociolek, Martin,Bennett, Jason,Casbohm, Jerry
, p. 540 - 544 (2014/06/09)
The bioreduction of N-oxide compounds is the basis for the mode of action of a number of biologically active molecules. These compounds are thought to act by forming a reactive oxygen species through an intracellular reduction and subsequent redox cycling process within the organism. With these results in mind, the preliminary investigation into the electrochemical reduction of the benzisoxazole 2-oxide ring system was undertaken, with the thought that this class of compounds would reduce in a similar fashion to other N-oxide heterocycles. The electrochemical reduction of 3-phenyl-1,2-benzisoxazole 2-oxide on boron-doped diamond was studied using cyclic and square wave voltammetry as well as controlled potential electrolysis and HPLC for qualitative identification of the reaction products. It was found that the reduction proceeded with an initial quasi-reversible one-electron reduction followed by the very fast cleavage of either the endocyclic or exocyclic N-O bond. Subsequent electron transfer and protonation resulted in an overall two-electron reduction and formation of the 2-hydroxyaryl oxime and benzisoxazole. These results are analogous to those observed in the electrochemical reduction of other heterocyclic N-oxides albeit the reduction of the benzisoxazole N-oxides takes place at a more negative potential. However, these encouraging results warrant further investigation into the reduction potential of substituted benzisoxazole N-oxides as well as to elucidate and characterize the nature of the intermediate species involved.
From antiferromagnetic to ferromagnetic exchange in a family of oxime-based MnIII dimers: A magneto-structural study
Barros, Wdeson P.,Inglis, Ross,Nichol, Gary S.,Rajeshkumar, Thayalan,Rajaraman, Gopalan,Piligkos, Stergios,Stumpf, Humberto O.,Brechin, Euan K.
, p. 16510 - 16517 (2013/12/04)
The reaction of Mn(ClO4)2·6H2O, a derivatised phenolic oxime (R-saoH2) and the ligand tris(2-pyridylmethyl)amine (tpa) in a basic alcoholic solution leads to the formation of a family of cluster compounds of general formula [Mn III2O(R-sao)(tpa)2](ClO4) 2 (1, R = H; 2, R = Me; 3, R = Et; 4, R = Ph). The structure is that of a simple, albeit asymmetric, dimer of two MnIII ions bridged through one μ-O2- ion and the -N-O- moiety of the phenolic oxime. Magnetometry reveals that the exchange interaction between the two Mn III ions in complexes 1, 3 and 4 is antiferromagnetic, but that for complex 2 is ferromagnetic. A theoretically developed magneto-structural correlation reveals that the dominant structural parameter influencing the sign and magnitude of the pairwise interaction is the dihedral Mn-O-N-Mn (torsion) angle. A linear correlation is found, with the magnitude of J varying significantly as the dihedral angle is altered. As the torsion angle increases the AF exchange decreases, matching the experimentally determined data. DFT calculations reveal that the dyzπ*dyz interaction decreases as the dihedral angle increases leading to ferromagnetic coupling at larger angles.
Synthesis and Spectral Data of (E) and (Z) Oximes of 2-Hydroxybenzophenone Derivatives
Kopczynski, T.,Krzyzanowska, Ewa,Olszanowski, A.
, p. 486 - 492 (2007/10/02)
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