Leaving group effect in the sulfonyl transfer reactions of aryl benzenesulfonates with Grignard reagents

EROĞLU F., KAHYA N. D., Erdik E.

REACTION KINETICS AND CATALYSIS LETTERS, vol.98, no.2, pp.365-373, 2009 (SCI-Expanded) identifier identifier

  • Publication Type: Article / Article
  • Volume: 98 Issue: 2
  • Publication Date: 2009
  • Doi Number: 10.1007/s11144-009-0053-x
  • Journal Name: REACTION KINETICS AND CATALYSIS LETTERS
  • Journal Indexes: Science Citation Index Expanded (SCI-EXPANDED), Scopus
  • Page Numbers: pp.365-373
  • Keywords: C-S coupling, Grignard reagents, Aryl arenesulfonates, Leaving group effect, NUCLEOPHILIC-SUBSTITUTION REACTIONS, MECHANISM, ARENESULFONATES, HYDROLYSIS, CATALYSTS, ESTERS
  • Ankara University Affiliated: Yes

Abstract

The C-S coupling reactions of aryl benzenesulfonates with phenylmagnesium bromide in THF:toluene (7:10) at 90 A degrees C have been studied. A Hammett-type kinetic study of the leaving group effect of aryloxy groups provides a conclusive support for a two step addition-elimination mechanism in which C-S bond formation is rate determining step.