The Journal of organic chemistry

Single-isomer iodochlorination of alkynes and chlorination of alkenes using tetrabutylammonium iodide and dichloroethane

ML Ho, AB Flynn, WW Ogilvie

Index: Ho, Michael L.; Flynn, Alison B.; Ogilvie, William W. Journal of Organic Chemistry, 2007 , vol. 72, # 3 p. 977 - 983

Full Text: HTML

Citation Number: 30

Abstract

The efficient formation of single-isomer, differentially halogenated alkenes and alkanes is described. These structures were generated by treatment of the appropriate alkyne or alkene with tetrabutylammonium iodide in refluxing dichloroethane. This process is highly selective as evidenced by control experiments using ICl. Treatment of the same alkenes and alkynes directly with iodine monochloride resulted in complex, inseparable mixtures of ...