Journal of the Korean Chemical Society (대한화학회지)

Korean Chemical Society (대한화학회)
권호 표지

Synthesis and Exploratory Photochemistry of ${\beta},\;{\gamma}$-unsaturated Carboxylic Acid, Carboxamide and Nitrile Derivatives

${\beta},\;{\gamma}$-불포화카르복시산, 카르복시아미드와 니트릴 유도체의 합성과 이들의 광화학적 반응에 관한 연구

  • Givens Richard S. (Chemistry Department, University of Kansas Lawrence) ;
  • Woo Ki Chae (Department of Chemistry, Chungbuk National University)
  • ;
  • 채우기 (충북대학교 자연과학대학 화학과)
  • Published : 1982.04.30
Download PDF
⟨ Previous Next ⟩

Abstract

The ketone chromophore of 1-Acetyl-1-methyl-2-cyclopentene (1) was replaced by nitrile, carboxylic acid and acetamide group, and their photochemical reactions were investigated. While the ${\beta},\;{\gamma}$-unsaturated ketone 1 afforded 1,2 ar 1,3-Acyl shift product, these replaced chromophores did not afford any monomeric rearranged products. 1-Cyano-1-methyl-2-cyclohexene also afforded no product anology of the 1,2-acyl shift reaction. The replacement of the ketone chromophore by nitrile, carboxylic acid and carboxamide has greatly altered the photochemistry of ${\beta},\;{\gamma}$-unsaturated ketones.

1-아세틸-1-메틸-2-시클로펜텐 화합물의 케톤 Chromophore를 나트릴, 카르보시산, 아미드 등의 group으로 대치하여 이들의 광화학반응을 검토한 결과 케튼 Chromophore에서 볼 수 있는 1,3-Acyl shift나 ODPM 반응은 일어나지 않았고 광화학적 중합 및 환원반응등 Chromophore를 변화시키므로서 광화학반응에 큰 변화를 보여주었다. 1-Cyano-1-methyl-2-cyclohexene의 경우도 Ketone chromophore와 비교하여 광화학 반응을 검토하였다.

Keywords

References

  1. Chem. Rev. v.76 K. N. Houk
  2. Ph. D. Dissertation, University of Kansas C. V. Neywick
  3. R. S. Givens;J. Liu
  4. Helv. Chim. Acta v.60 H. U. Gonzenbach;I. M. Tegmo-Larsson;J. P. Grosclaude;K. Schaffner
  5. Tetrahedron v.32 K. Schaffner
  6. Chem. Commun. v.75 C. Manning;J. J. McCullough
  7. J. Amer. Chem. Soc. v.88 H. E. Zimmerman;R. G. Lewis;J. J. McCullough;A. W. Padwa;S. W. Staley
  8. Org. Syn. Coll. v.II R. F. B. Cox;R. T. Stormont
  9. J. Amer. chem. Soc. v.78 O. H. Wheeler;I. Lerner
  10. Tetrahedron Lett. G. R. Kieczykowski;R. H. Schlessinger;R. B. Sulsky
  11. Tetrahedron Lett. M.W. Rathke;D. Sullivan
  12. Tetrahedron Lett. G. R. Kieczykowski;R. H. Schlessinger;R. B. Sulsky
  13. Tetrahedron Lett. N. Nakamura;K. Sakai
  14. J. Amer. Chem. Soc. v.86 E. J. Corey;R. B. Mitra