Add time:07/25/2019         Source:sciencedirect.com

The rates of the base-catalysed eliminations of a series of p-substituted phenyl β-chloroethyl sulfones have been determined in anhydrous acetonitrile using Et3N, Et2 NCH2CH2OH, EtN(CH2CH2OH)2 and N(CH2CH2OH)3 as the bases. The relative rates obtained with these amine bases were 550:52:6·6:1, respectively, depicting that the rates are correlated with the Brønsted basicities of these bases. The Hammett ϱ values obtained with p-substituted phenyl-β-chloroethyl sulfones for Et3N, 1·81, Et2NCH2CH2OH, 1·75, EtN(CH2CH2OH)2, 1·72 and N(CH2CH2OH)3, 1·64, suggest that the carbanionic character of the transition state increases with the increase of the base strength. β-Hydrogen kinetic isotope effects of β-phenylsulfonylethyl tosylate determined with these bases under the same reaction condition were found to be nearly identical (ca. 2·0). the transition states are discussed in the light of these observations.

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