Bulletin of the Korean Chemical Society

  • 제4권1호
  • /
  • Pages.41-44
  • /
  • 1983
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  • 0253-2964(pISSN)
  • /
  • 1229-5949(eISSN)
대한화학회 (Korean Chemical Society)
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MO Theoretical Studies on Stereoelectronic Control in the Addition Reaction of 1, 4-Benzoquinone-4-(O-methyloxime)$^*$

  • 발행 : 1983.02.20
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초록

The chlorine addition and Diels-Alder cycloaddition of cyclopentadiene to 1, 4-benzoquinone-4-(O-methyloxime) have been studied MO theoretically. It has been shown that the reactions occur predominantly to the quinone ring double bond which is oriented anti to the nitrogen lone pair due to an n-${\sigma}^*$ interaction between the nitrogen lone pair, n, and the app. vicinal bond, causing the ${\pi}$ bond to be weakened and destabilized due to the less conjugation from reduced delocalization.

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참고문헌

  1. J. Org. Chem. v.43 P. V. Alston;R. M. Ottenbrite;T. Cohen
  2. Spec. Pupl., The Chem. Soc., London Interatomic Distances L. E. Sutton
  3. Tetrahedron v.33 N. T. Anh;O. Eisenstein;J. M. Lefour
  4. Mechanism and Theory in Organic Chemistry T. H. Lowry;K. S. Richardson
  5. J. Org. Chem. v.46 J. E. Baldwin;R. K. Norris
  6. J. Korean Chem. Soc. v.26 Ikchoon Lee;Eun Sook Han;Keun Bae Ryhu
  7. Tetrahedron v.24 J. Feuer;W. C. Herndon;L. H. Hall
  8. Tetrahedron v.33 C. Minot;N. T. Anh
  9. J. Amer. Chem. Soc. v.98 R. E. Townsend;G. Ramunni;G. Segal;W. J. Hehre;L. Salem
  10. Theor. Chem. Acta. v.40 L. A. Burke;G. Leroy;M. Sana
  11. Structural Theory of Organic Chemistry N. D. Epiotis;W. R. Cherry;S. Shaik;R. L. Yates;F. Bernardi
  12. Approximate MO Theory J. A. Pople;D. L. Beverage
  13. Bull. Korean Chem. Soc. v.1 Ikchoon Lee
  14. Proc. Roy. Soc. London v.A284 J. N. Murrel;M. Randic;D. R. Williams
  15. Chemical Reactivity and Reaction Paths W. C. Herndon;J. Feuer;W. B. Giles;D. Otterson;E. Silber;Klopmann(ed.)
  16. Frontier Orbitals and Organic Chemical Reaction I. Fleming