View PDF Version
 
DOI: 10.1039/A901090D (Paper) Reference Section for: J. Chem. Soc., Perkin Trans. 1, 1999, 2391-2395

Photochemistry of chromones: photoreorganisation of 3-alkoxy-2-thienyl-4-oxo-4H-1-benzopyrans

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

Satish C. Gupta, Somesh Sharma, Ashok Saini and Som N. Dhawan

Abstract

Photoirradiation of a methanolic solution of 3-alkoxy-2-thienyl-4-oxo-4H-1-benzopyrans with Pyrex filtered UV light leads to cyclised and cyclodehydrogenated angular products involving both thiophene and alkoxy groups. The reaction is initiated through H-abstraction. The product distribution depends upon the substituents on the thiophene ring.

References

  1. A. Feigenbaum, Y. Fort, J. P. Pete and D. Scholler, J. Org. Chem., 1986, 51, 4424 CrossRef CAS; J. Cossy and J. P. Pete, Heterocycles, 1984, 22, 97 CAS; J. C. Arnould, J. Cossy and J. P. Pete, Tetrahedron, 1981, 37, 1921 CrossRef CAS; J. C. Arnould, A. Enger, A. Feigenbaum and J. P. Pete, Tetrahedron, 1979, 35, 2501 CrossRef CAS; A. Enger, A. Feignbaum, J. P. Pete and J. L. Wolfhugel, Tetrahedron, 1978, 34, 1509 CrossRef CAS; A. B. Smith, III and W. C. Agosta, J. Am. Chem. Soc., 1973, 95, 1961 CrossRef; W. C. Agosta and A. B. Smith, III, J. Am. Chem. Soc., 1971, 93, 5513 CrossRef CAS.
  2. S. C. Gupta, N. S. Yadav and S. N. Dhawan, J. Indian Chem. Soc., 1990, 67, 770 Search PubMed; S. C. Gupta and S. K. Mukherjee, Indian J. Chem., 1973, 11, 1263 Search PubMed.
  3. S. C. Gupta, A. Saini, D. Kumar, N. S. Yadav, K. Chand, S. Mor and S. N. Dhawan, J. Chem. Soc., Perkin Trans. 1, 1995, 177 RSC.
  4. S. C. Gupta, N. S. Yadav and S. N. Dhawan, Indian J. Chem., Sect. B, 1991, 30, 790.
  5. P. Mandal, A. Nath and R. V. Venkateswaran, Tetrahedron, 1996, 52, 7855 CrossRef CAS; S. C. Gupta and S. K. Mukerjee, Tetrahedron Lett., 1973, 5073 CrossRef CAS.
  6. H. Wynberg, H. V. Driel and J. Buler, J. Am. Chem. Soc., 1967, 89, 3492.
  7. S. W. Banks, M. J. Steele, D. Ward and P. M. Dewick, J. Chem. Soc., Chem. Commun., 1982, 156 Search PubMed; K. G. R. Pachler and W. G. E. Underwood, Tetrahedron, 1967, 23, 1817 CrossRef CAS.
  8. P. C. Model for Windows, Version 5.13, Serena Software.
  9. T. Matsuura and H. Matsushima, Tetrahedron, 1968, 24, 6615 CrossRef CAS; A. C. Waiss, R. E. Lundin, A. Lee and J. Corse, J. Am. Chem. Soc., 1967, 89, 6213 CrossRef CAS; A. C. Waiss and J. Corse, J. Am. Chem. Soc., 1965, 87, 2068 CrossRef CAS.
  10. J. Tirouflet and P. L. Cheng, Bull. Soc. Chim. Fr., 1963, 2252 CAS.
Click here to see how this site uses Cookies. View our privacy policy here.