Browsing by Author "Sands, Kai N."
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- ItemOpen AccessOne-Pot Synthesis of Aryl Selenonic Acids and some Unexpected Byproducts(ASC Publications, 2021-07-16) Sands, Kai N.; Gelfand, Benjamin S.; Back, Thomas G.The synthesis of aryl selenonic acids was achieved from diverse aryl bromides via a one-pot method involving metalation, selenation and oxidation with hydrogen peroxide, followed by ion exchange to afford the pure products in 77-90% yield. An o-hydroxymethyl derivative was found to dehydrate readily, affording the first example of a cyclic selenonic ester, while two minor byproducts were isolated and shown by x-ray crystallography to be mixed salts of aryl selenonic acids with either the corresponding aryl seleninic or selenious acid.
- ItemOpen AccessUnexpected Formation and Potent Antioxidant Activity of Macrocyclic Dimers Containing Disulfide and Selenide Groups(Wiley, 2022-11-17) McMillan, Jacob D.R.; Sands, Kai N.; Cooney, Gary S.; Gelfand, Benjamin S.; Back, Thomas G.During attempts to prepare spirodithiaselenuranes as GPx mimetics, a series of unexpected dimeric macrocycles was obtained, each containing two selenide and two disulfide moieties in rings ranging from 18- to 26-membered. The products showed potent GPx-like activity in an NMR assay based on their ability to catalyze the reduction of hydrogen peroxide with benzyl thiol. The high catalytic activity was attributed to transannular effects during selenide to selenoxide oxidation. This redox process was also characterized by an induction period that indicated autocatalysis in the formation of an intermediate selenoxide from the oxidation of the corresponding selenide.