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KMID : 1059519950390080643
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Journal of the Korean Chemical Society
1995 Volume.39 No. 8 p.643 ~ p.649
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Structure-Reactivity Relationship of Benzyl benzenesulfonates (Part 2). Nucleophilic Substitution Reaction of Benzyl Derivatives
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Chung Duck-Young
Kim Sung-Hong
Lee Myung-Ho
Yoh Soo-Dong
Fujio Mizu
Tsuno Yuho
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Abstract
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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℃ and 50℃. On the plot of kobs versus concentrations of nucleophile under pseudo-first order conditions, 3,4-(CH3O)2-benzyl bromide and 4-CH3O-benzyl bromide were a positive intercept at zero concentration of nucleophile. The k1 value for each compound was invariant with the different nucleoephile. However, 4-CH3- 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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KEYWORD
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