Structure-Reactivity Relationship of Benzyl benzenesulfonates (Part 2). Nucleophilic Substitution Reaction of Benzyl Derivatives

Benzyl benzenesulfonate류의 구조-반응성 관계 (2보). 벤질 유도체의 친핵성 치환반응

  • Cheong, Duk-Young (Department of Chemistry Education, Kyungpook National University) ;
  • Kim, Sung-Hong (Department of Chemistry Education, Kyungpook National University) ;
  • Lee, Myung-Ho (Department of Chemistry Education, Kyungpook National University) ;
  • Yoh, Soo-Dong (Department of Chemistry Education, Kyungpook National University) ;
  • Fujio, Mizue (Institute for Fundamental Research of Organic Chemistry, Kyushu University) ;
  • Tsuno, Yuho (Institute for Fundamental Research of Organic Chemistry, Kyushu University)
  • Published : 19950800

Abstract

The Menschutkin type reactions of substituted(Z)-benzyl systems with substituted(Y)-pyridines and N,N-dimethyl aniline have been studied by the electro-conductometric method in acetonitrile at 35$^{\circ}C$ and 50$^{\circ}C$. On the plot of $k_{obs}$ versus concentrations of nucleophile under pseudo-first order conditions, 3,$4-(CH_3/O)_2$-benzyl bromide and $4-CH_3O$-benzyl bromide were a positive intercept at zero concentration of nucleophile. The $k_1$ value for each compound was invariant with the different nucleoephile. However, $4-CH_3-$ and other electron withdrawing substituents of benzyl bromides did not show the positive intercept. These results are suggested that the reactions have been proceeding simultaneously and independently for the activated benzyl bromides via direct bimolecular and intimate ion pair intermediate.

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References

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