Fenner Tahli, White Jonathan M, Schiesser Carl H
School of Chemistry, The University of Melbourne, Victoria, Australia 3010.
Org Biomol Chem. 2006 Feb 7;4(3):466-74. doi: 10.1039/b515385a. Epub 2005 Dec 21.
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.
2-乙氧羰基-2-(2-(苄基硒基)吡啶-3-基)十三烷羧酸(20)的硫代肟酸酯衍生物21经光解，以89%的产率得到2-十二烷基-2-乙氧羰基-2,3-二氢硒并[2,3-b]吡啶(22)，该过程可能涉及叔烷基自由基在硒原子上进行分子内均裂取代并失去一个苄基自由基。另外，2-乙氧羰基-N-羟基吡啶-2-硒酮的O-(ω-卤代烷基)酯34重排，以79%的产率得到氮杂萘鎓卤化物37。
