Kinetics and mechanism of the C-S coupling reactions of aryl Grignard reagents with aryl arenesulfonates |
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Authors: | Ender Erdik Fatma Ero?lu |
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Institution: | (1) Ankara University, Science Faculty, Beşevler, Ankara, 06100, Turkey |
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Abstract: | The kinetics of the C-S coupling of arylmagnesium bromides with phenyl tosylate has been studied in THF: toluene at 90°C.
The reaction is first order in Grignard reagent and first order in phenyl tosylate. Kinetic data, Hammett relationship and
activation parameters are consistent with a nucleophilic addition mechanism involving rate determining attack of carbanion
to sulfonyl group followed by a fast phenoxide group leaving.
![MediaObjects/11532_2008_17_Fig1_HTML.jpg](/content/g123616440n0qm21/MediaObjects/11532_2008_17_Fig1_HTML.jpg) |
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Keywords: | Grignard reagents Aryl carbanions C-S coupling Hammett plot Activation parameters |
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