Bulletin of the Korean Chemical Society

Korean Chemical Society (대한화학회)
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Correlation of Chemical Shifts with Substituent Parameters in N-Benzyl Derivatives of Pyrrole,3a,7a-Dihydroindole,and Indole Esters

  • Published : 2002.09.20
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Abstract

Series of m- and p-substituted benzyl derivatives of pyrrole, tetramethyl 1-benzyl-3a,7a-dihydroindole-2,3,3a,4-tetracarboxylate, and trimethyl 1-benzylindole-2,3,4-tricarboxylate were prepared and their 13C NMR spectra were obtained in 0.1 M solutions of chloroform-d. Both single substituent parameter and dual substituent parameter analyses were carried out to correlate the substituent chemical shifts. The ${\beta}$ carbon of the indole series showed the most profound substituent effect dependence as well as the best correlation. The results are explained by the hyperconjugation of the benzyl methylene group.

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References

  1. Craik, D. J.; Brownlee, R. T. C. Prog. Phys. Org. Chem. 1983, 14, 1. https://doi.org/10.1002/9780470171936.ch1
  2. Slater, C. D.; Robinson, C. N.; Bies, R.; Bryan, D. W.; Chang, K.; Hill, A. W.; Moore, W. H., Jr.; Otey, T. G.; Popperlreiter, M. L.; Reisser, J. R.; Stablein, G. E.; Waddy, V. P. III; Wilkinson, W. O.; Wray, W. A. J. Org. Chem. 1985, 50, 4125. https://doi.org/10.1021/jo00221a031
  3. Suezawa, H.; Yuzuri, T.; Hirota, M.; Ito, Y.; Hanada, Y. Bull. Chem. Soc. Jpn. 1990, 63, 328. https://doi.org/10.1246/bcsj.63.328
  4. Yuzuri, T.; Suezawa, H.; Hirota, M. Bull. Chem. Soc. Jpn. 1994, 67, 1664. https://doi.org/10.1246/bcsj.67.1664
  5. Lee, C. K.; Yu, J. S.; Park, J. S. Bull. Korean Chem. Soc. 2000, 21, 49.
  6. Lee, C. K.; Jun, J. H.; Yu, J. S. J. Heterocyclic Chem. 2000, 37, 15. https://doi.org/10.1002/jhet.5570370104
  7. Acheson, R. M.; Vernon, J. M. J. Chem. Soc. 1962, 1142.
  8. Pretsch, E.; Buhlman, P.; Affolter, C. Structure Determination of Organic Compounds; Springer: Berlin, Germany, 2000; p 109.
  9. Carr, R. M.; Norman, R. O. C.; Vernon, J. M. J. Chem. Soc. Perkin Trans. I 1980, 156. https://doi.org/10.1039/p19800000156
  10. Ruff, F.; Csizmadia, I. G. Organic Reactions Equilibria, Kinetics and Mechanism; Elsevier: Amsterdam, 1994: p 164.
  11. Carey, F. A.; Sundberg, R. J. Advanced Organic Chemistry; Part A: Structure and Mechanism, 4th Ed.; Kluwer Academic/Plenum Pub.: New York, 2000; p 208.
  12. Robinson, C. N.; Stablein, G. E.; Slater, C. D. Tetrahedron 1990, 46, 335. https://doi.org/10.1016/S0040-4020(01)85418-1
  13. Bromilow, J.; Brownlee, R. T. C.; Craik, D. J.; Fiske, P. R.; Rowe, J. E.; Sedek, M. J. Chem. Soc. Perkin Trans. II 1981, 753.
  14. Ehrenson, S.; Brownlee, R. T. C.; Taft, R. W. Prog. Phys. Org. Chem. 1973, 10, 1. https://doi.org/10.1002/9780470171899.ch1

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