Organic & biomolecular chemistry

Preparation of 2, 3-dihydroselenolo [2, 3-b] pyridines and related compounds by free-radical means

T Fenner, JM White, CH Schiesser

文献索引：Fenner, Tahli; White, Jonathan M.; Schiesser, Carl H. Organic and Biomolecular Chemistry, 2006 , vol. 4, # 3 p. 466 - 474

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被引用次数: 19

摘要

Photolysis of the thiohydroximate ester derivative 21 of 2-carboethoxy-2-(2-(benzylseleno) pyridin-3-yl) tridecylcarboxylic acid (20) affords 2-dodecyl-2-carboethoxy-2, 3- dihydroselenolo [2, 3-b] pyridine (22) in 89% yield in a process presumably involving intramolecular homolytic substitution by a tertiary alkyl radical at selenium with loss of a benzyl radical. Alternatively, rearrangement of O-(ω-haloalkyl) esters 34 of 2-carboethoxy- ...