Preparation of 2,3-dihydroselenolo[2,3-b]pyridines and related compounds by free-radical means.
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-(omega-haloalkyl)esters 34 of 2-carboethoxy-N-hydroxypyridine-2-selone affords azonianaphthalenium halides 37 in 79% yield.
Fenner
Tahli
T
School of Chemistry, The University of Melbourne, Victoria, Australia 3010.
White
Jonathan M
JM
Schiesser
Carl H
CH
D004952:Esters / Q000737:chemistry; D005609:Free Radicals / Q000737:chemistry*; D006900:Hydroxylation; D015394:Molecular Structure; D010084:Oxidation-Reduction; D011725:Pyridines / Q000138:chemical synthesis* / Q000737:chemistry*; D012643:Selenium / Q000737:chemistry*
D004952:Esters; D005609:Free Radicals; D011725:Pyridines; D012643:Selenium; C023666:pyridine