Table of Contents
Organic Chemistry International
Volume 2010, Article ID 764185, 5 pages
http://dx.doi.org/10.1155/2010/764185
Research Article

Effect of a Strategically Positioned Methoxy Substituent on the Photochemistry of 3-Aryl-3H-1-Oxacyclopenta[l]Phenanthren-2-Ones

1Department of Applied Chemistry, Cochin University of Science and Technology, Kochi 682022, India
2Department of Chemistry and Biochemistry, University of Missouri-St. Louis, St. Louis, MO 63121, USA

Received 29 September 2010; Accepted 24 November 2010

Academic Editor: Dipakranjan Mal

Copyright © 2010 Roshini K. Thumpakara et al. This is an open access article distributed under the Creative Commons Attribution License, which permits unrestricted use, distribution, and reproduction in any medium, provided the original work is properly cited.

Linked References

  1. Y. S. Rao, “Recent advances in the chemistry of unsaturated lactones,” Chemical Reviews, vol. 76, no. 5, pp. 625–694, 1976. View at Google Scholar
  2. A. Padwa, T. Brookhart, D. Dehm, and G. Wubbels, “Migratory aptitude studies in the photochemical rearrangement of 2(5H)-furanones,” Journal of the American Chemical Society, vol. 100, no. 26, pp. 8247–8259, 1978. View at Google Scholar · View at Scopus
  3. K. R. Gopidas, D. R. Cyr, P. K. Das, and M. V. George, “Photochemical and thermal transformations of 3-benzyl-2(3H)-furanones and related substrates,” Journal of Organic Chemistry, vol. 52, no. 25, pp. 5505–5511, 1987. View at Google Scholar · View at Scopus
  4. S. Pratapan, K. Ashok, D. R. Cyr, P. K. Das, and M. V. George, “Substituent effects in the photochemistry of 5-aryl-3,3-diphenyl-2(3H)-furanones. Steady-state and laser flash photolysis studies,” Journal of Organic Chemistry, vol. 53, no. 25, pp. 5826–5831, 1988. View at Google Scholar · View at Scopus
  5. L. Fillol, M. A. Miranda, I. M. Morera, and H. Sheikh, “Photochemistry of 2(3H)- and 2(5H)-furanones,” Heterocycles, vol. 31, no. 4, pp. 751–782, 1990. View at Google Scholar · View at Scopus
  6. O. L. Chapman and C. L. McIntosh, “Photochemical decarbonylation of unsaturated lactones and carbonates,” Journal of the Chemical Society D, no. 8, pp. 383–384, 1971. View at Publisher · View at Google Scholar · View at Scopus
  7. R. Martinez-Utrilla and A. M. Miranda, “Photochemistry of 5-aryl-2(3H)-furanones. : A new route to the synthesis of chromones,” Tetrahedron, vol. 37, pp. 2111–2114, 1981. View at Google Scholar
  8. S. Breda, I. Reva, and R. Fausto, “UV-induced unimolecular photochemistry of 2(5H)-furanone and 2(5H)-thiophenone isolated in low temperature inert matrices,” Vibrational Spectroscopy, vol. 50, no. 1, pp. 57–67, 2009. View at Publisher · View at Google Scholar · View at Scopus
  9. A. Yogev and Y. Mazur, “Irradiation of enol lactones,” Journal of the American Chemical Society, vol. 87, no. 15, pp. 3520–3521, 1965. View at Google Scholar · View at Scopus
  10. C. D. Gutsche and B. A. M. Oude-Alink, “The photoinduced alcoholysis of 3,4-dihydrocoumarin and related compounds,” Journal of the American Chemical Society, vol. 90, no. 21, pp. 5855–5861, 1968. View at Google Scholar · View at Scopus
  11. I. S. Krull and D. R. Arnold, “The Hg senitized vapor phase photolysis of γ-crotonolactone and simple butenolides,” Tetrahedron Letters, vol. 25, no. 16, pp. 1247–1249, 1969. View at Google Scholar
  12. G. Rio and J. C. Hardy, “Triphenyl-3,4,5 H-5 furannone-2, acide cis-benzoyl-3 diphenyl-2,3 acrylique et derives,” Bulletin de la Societe Chimique de France, vol. 10, pp. 3572–3578, 1970. View at Google Scholar
  13. B. B. Lohray, C. V. Kumar, P. K. Das, and M. V. George, “Photochemical and thermal transformations of 2(3H)-furanones and bis(benzofuranones). A laser flash photolysis study,” Journal of the American Chemical Society, vol. 106, no. 24, pp. 7352–7359, 1984. View at Google Scholar · View at Scopus
  14. K. R. Gopidas, B. B. Lohray, S. Rajadurai, P. K. Das, and M. V. George, “Sensitized photorearrangement of 3,3,5-triaryl-2(3H)-furanones to 3,4,5-triaryl-2(5H)-furanones. Steady-state and laser flash photolysis investigations,” Journal of Organic Chemistry, vol. 52, no. 13, pp. 2831–2838, 1987. View at Google Scholar · View at Scopus
  15. G. Rio and J. C. Hardy, “Triphenyl-3,4,5 H-5 furannone-2, acide cis- benzoyl-3 diphenyl-2,3 acrylique et derives,” Bulletin de la Societe Chimique de France, vol. 10, pp. 3572–3578, 1970. View at Google Scholar
  16. P. J. Wagner and R. G. Zepp, “γ- vs. δ-Hydrogen abstraction in the photochemistry of β-alkoxy ketones. An overlooked reaction of hydroxy biradicals,” Journal of the American Chemical Society, vol. 93, no. 19, pp. 4958–4959, 1971. View at Google Scholar · View at Scopus
  17. A. M. Jacob, R. K. Thumpakkara, S. Prathapan, and B. Jose, “Synthesis of 3,3-dimethoxy-2-aryl-2,3-dihydro-1-oxa-cyclopenta[l] phenanthren-2-ols and their conversion to 2(3H)- and 3(2H)-furanones,” Tetrahedron, vol. 61, no. 19, pp. 4601–4607, 2005. View at Publisher · View at Google Scholar · View at Scopus