Theoretical Studies on the Diels-Alder Reactions between Cyclopentadiene and Conformationally Flexible Dienophiles

시클로 펜타디엔과 구조적으로 회전이 쉬운 Dienophile간의 Diels-Alder 반응에 대한 이론적 연구

  • 김찬경 (인하대학교 이과대학 화학과) ;
  • 이인영 (인하대학교 이과대학 화학과) ;
  • 이본수 (인하대학교 이과대학 화학과) ;
  • 이익춘 (인하대학교 이과대학 화학과) ;
  • 김관수 (연세대학교 이과대학 화학과) ;
  • 주영협 (연세대학교 이과대학 화학과)
  • Published : 19960700

Abstract

Dieis-Alder reaction between cyclopentadiene and 5-membered ring compounds which have exo-cyclic double bond has been studied using the PM3 method. Transition states do not show large geometrical change with the variation of dienophiles. Two isomers are possible due to the rotation of the exo-cyclic double bond of a dienophile. The reactivity for the formation of different products are explained using the FMO energy gap. The exo and endo selectivity of the reaction has been also studied from the correlation between the deformation energy and the activation barrier. Minimum energy reaction path is discussed using the Curtin-Hammett principle.

Keywords

References

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