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Nucleophilic Substitution Reactions of 1- and 2-Naphtylmethyl Arenesulfonates with Anilines

  • 발행 : 1997.02.20

초록

Kinetic studies are carried out on the reactions of 1- and 2-naphthylmethyl arenesulfonates with anilines in acetonitrile at 25.0 ℃. The rates are faster for the 2-naphthylmethyl series than for the corresponding 1-naphthylmethyl series suggesting that there is a greater stabilization of positive charge development in the TS at the arylmethyl reaction center carbon for the former. The sign and magnitude of ρxz (=-0.12) are similar to those of the benzylic series. Thus, benzyl, 1- and 2-naphthylmethyl derivatives belong to a class of compounds which react with aniline nucleophiles through a relatively loose SN2 TS. Kinetic secondary deuterium isotope effects indicated that a stronger nucleophile and nucleofuge lead to a later TS as the definition of ρxz requires.

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참고문헌

  1. Chem. Soc. Rev. v.19 Lee, I.
  2. Adv. Phys. Org. Chem. v.27 Lee, I.
  3. Chem. Soc. Rev. v.24 Lee, I.
  4. J. Chem. Soc., Perkin Trans v.2 Lee, I.;Koh, H. J.;Lee, B. S.;Sohn, D. S.;Lee, B. C.
  5. J. Org. Chem. v.59 Lee, I.;Kim, C. K.;Chung, D. S.;Lee, B. S.
  6. Bull Korean Chem. Soc. v.16 Oh, H. K.;Kwon, Y. B.;Chung, D. S.;Lee, I.
  7. J. Phys. Org. Chem. v.9 Oh, H. K.;Kwon, Y. B.;Chung, D. S.;Lee, I.
  8. Bull. Inst. Basic Sci. Inha University v.12 Lee, I.;Lee, W. H.;Jung, H. J.
  9. Tetrahedron v.41 Lee, I.;Lee, H. W.;Sohn, S. C.;Kim, C. S.
  10. J. Chem. Soc. Perkin Trans v.2 Lee, I.;Sohn, S. C.;Kang, C. H.;Oh, Y. J.
  11. Tetrahedron v.42 Lee, I.;Sohn, S. C.;Oh, Y. J.;Lee, B. C.
  12. The MO theory of Organic Chemistry Dewar, M. J. S.
  13. The PMO theory of Organic Chemistry Dewar, M. J. S.;Dougherty, R. C.
  14. J. Am. Chem. Soc. v.104 Hoffman, R. V.;Belfoure, E. L.
  15. J. Am. Chem. Soc. v.108 Hoffman, R. V.;Shankweiler, J. M.
  16. J. Am. Chem. Soc. v.92 Bentley, M. D.;Dewar, M. J. S.
  17. J. Am. Chem. Soc. v.109 Lee, I.;Kang, H. K.;Lee, H. W.