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

The C–S coupling reactions of aryl benzenesulfonates with phenylmagnesium bromide in THF:toluene (7:10) at 90 °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...

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Bibliographic Details
Published inReaction kinetics and catalysis letters Vol. 98; no. 2; pp. 365 - 373
Main Authors Eroğlu, Fatma, Kâhya, Didem, Erdik, Ender
Format Journal Article
LanguageEnglish
Published Dordrecht Springer Netherlands 01.12.2009
Subjects
Catalysis
Chemistry
Chemistry and Materials Science
Industrial Chemistry/Chemical Engineering
Physical Chemistry
Grignard reagents
C–S coupling
Aryl arenesulfonates
Leaving group effect
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Summary:The C–S coupling reactions of aryl benzenesulfonates with phenylmagnesium bromide in THF:toluene (7:10) at 90 °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.
ISSN:0133-1736
1588-2837
DOI:10.1007/s11144-009-0053-x