The Reaction of Benzyl Arenesulfonate with N,N-Dimethylanilines (III). Substituent Effects of Leaving Group for Benzyl Arenesulfonate

Benzyl Arenesulfonate와 N,N-디메틸아닐린과의 反應 (第3報). Benzyl Arenesulfonate의 難脫基의 置換基 效果

  • Soo-Dong Yoh (Department of Chemistry, Teacher's College, Kyungpook National University)
  • 여수동 (慶北大學敎 師範大學 化學科)
  • Published : 1975.12.30

Abstract

Substituent effect of the leaving groups of the reaction of benzyl arenesulfonate with dimethylanilines in acetone at $35^{\circ}C$ was obtained with the following results. 1. Substituent effect of the leaving groups was not variable when changed from pyridine to N,N-dimethylaniline in nucleophile 2.In acetone, the Hammett ${\sigma}$ constant of p-MeO of the leaving group was -0.35. 3. The weaker the nucleophilicity in dimethylaniline, the stronger the movement of electron from N to C, and the cleavage of the C${\ldots}$0 bond in transition state proceeds.

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