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Stable Boron Peroxides with a Subporphyrinato Ligand
Author(s) -
Tsurumaki Eiji,
Sung Jooyoung,
Kim Dongho,
Osuka Atsuhiro
Publication year - 2016
Publication title -
angewandte chemie international edition
Language(s) - English
Resource type - Journals
SCImago Journal Rank - 5.831
H-Index - 550
eISSN - 1521-3773
pISSN - 1433-7851
DOI - 10.1002/anie.201511590
Subject(s) - chemistry , boron , triphenylphosphine oxide , methoxide , triphenylphosphine , ligand (biochemistry) , inorganic chemistry , single crystal , photochemistry , catalysis , polymer chemistry , organic chemistry , crystallography , biochemistry , receptor
Subporphyrin B‐peroxides have been synthesized in good yields by acid‐catalyzed exchange reactions of subporphyrin B‐methoxide with the corresponding hydroperoxides. Thermal dimerization of the subporphyrin B‐hydroperoxide provided the peroxo‐bridged bis(subporphyrin) quantitatively. These subporphyrin B‐peroxides are fairly stable under ambient conditions, which allowed their isolation and full characterization as the first examples of structurally authenticated boron hydroperoxides, acyclic boron organylperoxides, and neutral peroxo‐bridged diboron species. The subporphyrin B‐peroxides thus prepared were investigated through their crystal structures, IR spectra, and cyclic voltammograms as well as by DFT calculations. The subporphyrin B‐hydroperoxide oxidizes triphenylphosphine quantitatively to triphenylphosphine oxide.