Bulletin of the Korean Chemical Society

Korean Chemical Society (대한화학회)
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MINDO/3 Theoretical Studies on Sigmatropic Hydrogen Rearrangements (Ⅱ): Systems with Central Nitrogen Atom$^*$

  • Cho, Jeoung-Ki (Department of Chemistry, Inha Univerisity) ;
  • Lee, Ik-Choon (Department of Chemistry, Inha Univerisity) ;
  • Oh, Hyuck-Keun (Department of Chemistry, Jeonbuk National University) ;
  • Cho, In-Ho (Department of Chemistry, Jeonbuk National University)
  • Published : 1984.10.20
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Abstract

MINDO/3 theoretical studies were carried out on sigmatropic hydrogen rearrangements in systems with central nitrogen atom; three systems studied being (1) N-methylformaldimine, (2) nitrous acid, and (3) formaldoxime-nitrosomethane systems. It was found that in system (1), 1,3-H shift is preferred whereas in systems (2) and (3), 1,2-H shifts are favored. The relative order of reactivity for the three systems was found to be (2) < (3) < (1), which is exactly the opposite to that found for the corresponding systems with central carbon atom.

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References

  1. J. Comput. Chem. I. Lee;J. K. Cho;B-S. Lee
  2. J. Amer. Chem. Soc. v.77 G. S. Hammond
  3. J. Amer. Chem. Soc. v.100 T. J. Zielinski;D. L. Breen;Rein
  4. J. Amer. Chem. Soc. v.100 G. Klopman;P. Andreozzi;A. J. Hopfinger;O. Kikuchi;M. J. S. Dewar
  5. J. Korean Chem. Soc. J. K. Cho;I. Lee;H. K. Oh;I. H. Cho
  6. J. Amer. Chem. Soc. v.97 R. C. Bingham;M. J. S. Dewar;D. M. Lo
  7. QCPE v.10 M. L. Olson;J. F. Chiang
  8. Bull. Korean Chem. Soc. v.1 I. Lee
  9. J. Amer. Chem. Soc. v.100 L. R. Larson;N. D. Epiotis;F. Bernardi
  10. J. Amer. Chem. Soc. v.94 L. Radom;W. J. Hehre;J. A. Pople
  11. J. Amer. Chem. Soc. v.93 L. Radom;W. J. Hehre;J. A. Pople
  12. J. Amer. Chem. Soc. v.102 P. D. Adeney;W. J. Bouma;L. Radom;W. R. Rodwell