Selenium-catalyzed halolactonization: nucleophilic activation of electrophilic halogenating reagents.
Diphenyl diselenide catalyzes the halolactonization of unsaturated acids with N-halosuccinimides under mild conditions. The diselenide not only accelerates the reactions, but in some cases affords regiocontrol in favor of gamma-lactone products. Experiments show that the regioselectivity in favor of gamma-lactones is a result of kinetic rather than thermodynamic control.
Mellegaard
Shelli R
SR
Department of Chemistry, University of Kansas, Lawrence, KS 66045, USA.
Tunge
Jon A
JA
D002384:Catalysis; D005231:Fatty Acids, Unsaturated / Q000138:chemical synthesis* / Q000737:chemistry; D007700:Kinetics; D007783:Lactones / Q000138:chemical synthesis / Q000737:chemistry*; D015394:Molecular Structure; D012643:Selenium / Q000737:chemistry*; D013237:Stereoisomerism; D013388:Succinimides / Q000138:chemical synthesis / Q000737:chemistry*
D005231:Fatty Acids, Unsaturated; D007783:Lactones; D013388:Succinimides; D012643:Selenium