Bulletin of the Korean Chemical Society

Korean Chemical Society (대한화학회)
권호 표지
DOI QR코드

DOI QR Code

cis-trans Isomeric and Substituent Effects on the Lanthanide Induced Shifts in 2-Phenylcyclopropanic System

  • So, Jung-Ho (Department of Chemistry, College of Sciences, Chungnam National University) ;
  • Cho, Nam-Sook (Department of Chemistry, College of Sciences, Chungnam National University)
  • Published : 1984.12.20
Download PDF
⟨ Previous Next ⟩

Abstract

LIS's of cis and trans-methyl-2-phenylcyclopropanecarboxylate, cis and trans-t-butyl-2-phenylcyclopropanecarboxylate, cis and trans-N,N-dimethylcyclopropanecarboxamide, trans-2-phenylcyclopropyl methyl ketone and trans-2-phenylcyclopropyl t-butyl ketone have been studied. The LIS's hold the McConnell-Robertson relation and are mainly influenced by the steric effect. LIS's of trans isomers are larger than those of cis isomers. In trans isomers, the LIS's decrease in the following order: methyl ketone > methyl ester > N,N-dimethyl amide > t-butyl ketone${\sim}$t-butyl ester.

Keywords

References

  1. J. Amer. Chem. Soc. v.91 C. C. Hinckley
  2. Chem. Rev. v.73 A. F. Cockerill;G. L. O. Davis;R. C. Harden;D. M. Rackram
  3. Top. Stereochem. v.10 Glenn Sullivan
  4. Adrichim. Acta v.10 K. A. Kime;R. E. Sievers
  5. Annu. Rep. NMR Spectrosc. v.6A G. A. Webb
  6. Science v.190 M. R. Willcott, III;R. E. Davis
  7. Handb. Phys. Chem. Rare Earths v.4 J. Reuben;G. Elgavish
  8. J. Org. Chem. v.46 J. A. Peters;P. J. Wijnand Schuyl;Wim M. M. J. Bovee;J. Henk Alberts;Herman Van Bekkum
  9. J. Amer. Chem. Soc. v.102 Douglas J. Raber;Christopher M. Janks;Miltion D. Johnston, Jr.;Nancy K. Raber
  10. J. Org. Chem. v.44 David J. H. Smith;John D. Finlay;C. Richard Hall;J. J. Uebel
  11. J. Org. Chem. v.43 Douglas J. Raber;Milton D. Johnston;Joseph W. Perry;George F. Jackson III
  12. J. Org. Chem. v.46 Douglas J. Raber;Christopher M. Janks;Miltion D. Johnston, Jr.;Michael A. Schwalke;B. L. Shapiro;G. L. Behelfer
  13. J. Amer. Chem. Soc. v.105 Ronald L. Bassfield
  14. J. Amer. Chem. Soc. v.105 Mangal Singh;Joe J. Reynolds;A. Dean Sherry
  15. J. Chem. Phys. v.29 H. M. McConnell;R. E. Robertson
  16. J. Amer. Chem. Soc. v.98 M. D. Johnston, Jr.;D. J. Raber;N. K. Degennaro;A. D. Angelo;J. W. Perry
  17. J. Amer. Chem. Soc. v.98 Glenn R. Sullivon
  18. Tetrahedron Lett. v.30 T. Aratani;Y. Yonaoshi;T. Nagas
  19. J. Org. Chem. v.29 C. H. Depuy;C. M. Dappen;K. L. Eilers;R. A. Klein
  20. J. Org. Chem. v.18 G. Montaudo;P. Maravigna;S. Cacamese;V. Librando
  21. Org. Magn. Resonance v.3 K. Spoargaren;P. K. Korver;P. J. Van der Haak;T. J. De Boer
  22. Org. Syn. Coll. v.IV A. H. Ford-Moore
  23. J. Amer. Chem. Soc. v.78 Akira Nakamura;Akira Konishi;Yoshitaka Tatsuno;Sei Otsuka
  24. J. Org. Chem. v.43 Paul E. Kreiger;John A. Landgrebe
  25. J. Org. Chem. v.45 Andre J. Anciaux;Ander J. Hubert;Alfred F. Noels;N. Petiniot;Phillippe Teyssie
  26. J. Org. Chem. v.39 Bernard Shapiro;Milton D. Johnston, Jr.;Michael J. Shapiro
  27. Teterahedron Lett. C. Beaute;Z.W. Wolkowshi;J. P. Merde;D. Lelandis
  28. J. Org. Chem. v.37 G. Montaudo;P. Finocchiaro
  29. Chem. Commun. C. Beaute;Z.W. Wolkowshi;N. Thoai
  30. J. Amer. Chem. Soc. v.102 Douglas J. Rader;Christopher M. Janks;Milton D. Jonston, Jr.;Nancy K. Raber
  31. Anal. Chem. v.47 J. P. Shoffner
  32. CRC Handbook of Chem. and Phy.
  33. J. Amer. Chem. Soc. v.97 M. D. Johnston, Jr.;B. L. Shapiro;M. J. Shapiro;T. W. proulx;A. D. Godwin;H. L. Pearce

Cited by

  1. NMR-based Enantiodifferentiation of Chiral trans-2-Phenylcyclopropane Derivatives Using a Chiral Lanthanide Shift Reagent vol.32, pp.6, 2011, https://doi.org/10.5012/bkcs.2011.32.6.2076