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Issue 11, 1973
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Elimination reactions on the borderline between concerted and stepwise processes. Base-promoted dehydrohalogenation of 2-phenylsulphonylethyl bromide, chloride, and fluoride

Vito Fiandanese,  Giuseppe Marchese  and  Francesco Naso 

Abstract

The reactions of 2-phenylsulphonylethyl bromide, chloride, and fluoride with methoxide ion in methanol and with triethylamine in acetonitrile and in benzene, have been followed kinetically. The reactivity order Br > Cl > F has been observed. The kinetic isotope effects were determined for the nine substrate–base–solvent combinations. The measured kH/kD values range from a maximum of 5·0 in the case of the bromo-derivative in alcohol to a minimum of 1·0 in the case of the fluoro-derivative in benzene. On the basis of isotope effects, leaving group effects, and related observations the position of the elimination mechanism in the E2–E1 cB spectrum is tentatively located.

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Article type: Paper
DOI: 10.1039/P29730001538
Citation: J. Chem. Soc., Perkin Trans. 2, 1973,0, 1538-1542
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    Elimination reactions on the borderline between concerted and stepwise processes. Base-promoted dehydrohalogenation of 2-phenylsulphonylethyl bromide, chloride, and fluoride

    V. Fiandanese, G. Marchese and F. Naso, J. Chem. Soc., Perkin Trans. 2, 1973, 0, 1538
    DOI: 10.1039/P29730001538

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