The Regio- and Stereo-chemistries of the (2π+2π) Photocycloaddition of Electron-deficient Ethenes to Isoquinolin-1(2H)-one

(Note: The full text of this document is currently only available in the PDF Version )

Nader Al-Jalal, Christopher Covell and Andrew Gilbert


Abstract

The (2π+2π) photocycloaddition of isoquinolin-1(2H)-one to electron-deficient ethenes is efficient, regiospecific and highly stereoselective: 254nm irradiation of the acrylonitrile adduct induces retroadditon and rearrangement to an N-vinylisoindolinone with equal efficiencies.


References

  1. G. R. Evanega and D. L. Fabiny, Tetrahedron Lett., 1971, 1749 CrossRef CAS.
  2. T. Naito and C. Kaneko, Chem. Pharm. Bull., 1985, 33, 5328 CAS.
  3. T. Naito and C. Kaneko, Tetrahedron Lett., 1981, 2671 CrossRef CAS.
  4. H. Suginome, Y. Kajizuka, M. Suzuki, H. Senboku and K. Kobayashi, Heterocycles, 1994, 37, 283 CAS.
  5. T. Chiba, Y. Takada, T. Naito and C. Kaneko, Chem. Pharm. Bull., 1990, 38, 2335 CAS.
  6. T. Chiba, Y. Takada, C. Kaneko, F. Kiuchi and Y. Tsuda, Chem. Pharm. Bull., 1990, 38, 3317 CAS.
  7. C. Kaneko, N. Katagiri, K. Uchiyama and T. Yamada, Chem. Pharm. Bull., 1985, 33, 4160 CAS.
  8. N. Al-Jalal, M. G. B. Drew and A. Gilbert, J. Chem. Soc., Perkin Trans. 1, 1996, 965 RSC.
Click here to see how this site uses Cookies. View our privacy policy here.