Tetrahedron

Homolytic substitution at selenium: ring closure of ω-(benzylseleno) alkyl radicals

LJ Benjamin, CH Schiesser, K Sutej

Index: Benjamin, Lynda J.; Schiesser, Carl H.; Sutej, Katarina Tetrahedron, 1993 , vol. 49, # 12 p. 2557 - 2566

Full Text: HTML

Citation Number: 43

Abstract

The ring closure of a series of ω-(benzylseleno) alkyl radicals (1) has been studied. Thiohydroxamic esters derived from ω-(benzylseleno) alkanoic acids decompose smoothly, upon irradiation, with the loss of carbon dioxide to afford 5–and 6–membered selenium- containing rings in 78–95% yield. The thiohydroxamic ester derived from 7-(benzylseleno) heptanoic acid affords the 7-membered heterocycle, selenopane in approximately 50% ...