Efficiency of alkoxyl radical product formation from 5-substituted 3-alkoxy-4-methylthiazole-2(3H)-thiones |
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Authors: | Jens Hartung Christine Schur Thomas Gottwald |
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Affiliation: | a Fachbereich Chemie, Organische Chemie, Technische Universität Kaiserslautern, Erwin-Schrödinger-Straße, D-67663 Kaiserslautern, Germany b Institut für Organische Chemie, Universität Würzburg, Am Hubland, 97074 Würzburg, Germany |
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Abstract: | In a comparative study, reactions between 5-(p-methoxyphenyl)-substituted 3-alkoxy-4-methylthiazole-2(3H)-thiones and appropriate mediators (BrCCl3, Bu3SnH) provided higher yields of alkoxyl radical products (δ-bromohydrins, cyclic ethers, carbonyl compounds) than respective transformations of 5-phenyl- and 5-methyl-substituted derivatives. The unusual selectivity of applied thiohydroxamates to furnish products of O-alkylation, even upon treatment with soft carbon electrophiles, and the marked propensity of 3-alkoxy-5-(p-methoxyphenyl)-4-methylthiazole-2(3H)-thiones to crystallize, facilitated preparation and purification of the new family of alkoxyl radical precursors in a noteworthy manner. |
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Keywords: | Addition Ambident nucleophile Bicyclic ether Bromohydrin C,H-Activation Carbohydrate Cyclization Fragmentation Substitution Tetrahydrofuran Thiazolethione Thiohydroxamate salt |
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