Selenium-catalyzed halolactonization: nucleophilic activation of electrophilic halogenating reagents

Shelli R Mellegaard; Jon A Tunge

doi:10.1021/jo048460o

Selenium-catalyzed halolactonization: nucleophilic activation of electrophilic halogenating reagents

J Org Chem. 2004 Dec 10;69(25):8979-81. doi: 10.1021/jo048460o.

Authors

Shelli R Mellegaard¹, Jon A Tunge

Affiliation

¹ Department of Chemistry, University of Kansas, Lawrence, KS 66045, USA.

PMID: 15575789
DOI: 10.1021/jo048460o

Abstract

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.

Publication types

Research Support, U.S. Gov't, Non-P.H.S.

MeSH terms

Catalysis
Fatty Acids, Unsaturated / chemical synthesis*
Fatty Acids, Unsaturated / chemistry
Kinetics
Lactones / chemical synthesis
Lactones / chemistry*
Molecular Structure
Selenium / chemistry*
Stereoisomerism
Succinimides / chemical synthesis
Succinimides / chemistry*

Substances

Fatty Acids, Unsaturated
Lactones
Succinimides
Selenium