View PDF Version
 
DOI: 10.1039/A903516H (Paper) Reference Section for: J. Chem. Soc., Perkin Trans. 1, 1999, 2507-2512

Photooxygenation (1O2) of silyl enol ethers derived from indan-1-ones: competitive formation of tricyclic 3-siloxy-1,2-dioxetane and α-silylperoxy ketone

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

Hiroyuki Einaga, Masatomo Nojima and Manabu Abe

Abstract

Photooxygenation (1O2) of silyl enol ethers 1 (X = H) and 2 (X = OMe) derived from indan-1-ones has been investigated. The oxygenation of silyl enol ethers 1 (X = H) was found to give the corresponding tricyclic 3-siloxy-1,2-dioxetanes 3 quantitatively. Alternatively, the silyl enol ethers 2 (X = OMe) gave tricyclic dioxetanes 6 together with α-silylperoxy ketones 7. The substituent effects of X = OMe on the direct formation of α-silylperoxy ketone 7 are explained by the formation of the 1,4-zwitterion intermediates (ZI). Thermolysis of the tricyclic 3-siloxy-1,2-dioxetanes 3 and 6 was observed for the first time to yield the keto esters 4 and 8, respectively.

References

  1. (a) Singlet Oxygen, eds. B. Ranby and J. F. Rabek, Wiley, Chichester, 1978 Search PubMed; (b) Singlet Oxygen, eds. H. H. Wasserman and R. W. Murray, Academic Press, New York, 1979 Search PubMed.
  2. (a) For reviews, see; K. Gollnick, Singlet Oxygen, eds. B. Ranby and J. F. Rabek, Wiley, Chichester, 1978, p. 110 Search PubMed; (b) K. Gollnick and H. J. Kuhn, Singlet Oxygen, eds. H. H. Wasserman and R. W. Murray, Academic Press, New York, 1979, p. 287 Search PubMed; (c) A. G. Griesbeck, Organic Photochemistry and Photobiology, eds. W. M. Horspool and P.-S. Song, CRC Press, Boca Raton, 1994, p. 301 Search PubMed; (d) M. Prein and W. Adam, Angew. Chem., Int. Ed. Engl., 1996, 35, 477 CrossRef CAS.
  3. (a) G. M. Rubottom and M. I. L. Nieves, Tetrahedron Lett., 1972, 2443; (b) E. Friedrich and W. Lutz, Angew. Chem., Int. Ed. Engl., 1977, 16, 413 CrossRef; (c) E. Friedlich and W. Lutz, Chem. Ber., 1980, 113, 1245; (d) G. R. Clark, M. M. Nikaido, C. K. Fair and J. Lin, J. Org. Chem., 1985, 50, 1994 CrossRef CAS.
  4. (a) W. Adam and H. C. Steinmetzer, Angew. Chem., Int. Ed. Engl., 1972, 11, 540 CAS; (b) W. Adam and J.-C. Lin, J. Am. Chem. Soc., 1972, 94, 2894 CrossRef CAS; (c) W. Adam, A. Alzerreca, J.-C. Lin and F. Yang, J. Am. Chem. Soc., 1977, 31, 1245; (d) W. Adam and X.-H. Wang, Tetrahedron Lett., 1990, 31, 1245 CrossRef CAS; (e) W. Adam, E. Kades and X.-H. Wang, J. Org. Chem., 1991, 56, 4737 CrossRef CAS.
  5. For example, see G. Stork and P. F. Hudrlik, J. Am. Chem. Soc., 1968, 90, 4462 Search PubMed.
  6. See ref. 2c..
  7. K. R. Kopecky, Chemical and Biological Generation of Electronically Excited States, eds. G. Cilento and W. Adam, Academic Press, Orlando, 1982, ch. 3, p. 85 Search PubMed.
  8. A. L. Baumstark, Advances in Oxygenated Processes, ed. A. L. Baumstark, JAI Press, Stamford, CT, USA, 1988, vol. 1, p. 31 Search PubMed.
  9. (a) Mechanistic work for the decomposition of 1,2-dioxetanes, see; ref. 8; (b) K. Yamaguchi, K. Takada, Y. Otsuji and K. Mizuno, Organic Peroxides, ed. W. Ando, Wiley, Chichester, 1992, p. 76 Search PubMed; (c) N. J. Turro and P. Lechtken, Pure Appl. Chem., 1973, 33, 363 CrossRef CAS; (d) D. R. Kearns, Chem. Rev., 1971, 71, 395 CrossRef CAS; (e) W. Adam and W. J. Boader, J. Am. Chem. Soc., 1985, 107, 410 CrossRef CAS; (f) W. H. Richardson, M. B. Lovett and L. Olson, J. Org. Chem., 1989, 54, 3523 CrossRef CAS.
  10. (a) Experimental evidence for the formation of perepoxides in 1O2 reaction with olefins, see; A. P. Schaap, S. G. Recher, G. R. Faler and S. R. Villasenor, J. Am. Chem. Soc., 1983, 105, 1691 Search PubMed; (b) T. H. W. Poon, K. Pringle and C. S. Foote, J. Am. Chem. Soc., 1995, 117, 7611 CrossRef CAS.
  11. The 1,4-zwitterionic intermediate was reported by Jefford; (a) C. W. Jefford and C. G. Rimbault, Tetrahedron Lett., 1977, 2375 CrossRef CAS; (b) C. W. Jefford, D. Jaggi, J. Boukouvalas and S. Kohmoto, J. Am. Chem. Soc., 1983, 105, 6497 CrossRef; (c) C. W. Jefford, S. Kohmoto, J. Boukouvalas and U. Burger, J. Am. Chem. Soc., 1983, 105, 6498 CrossRef.
  12. (a) A. R. Bassindale and P. G. Tayler, The Chemistry of Organic Silicon Compounds, eds. S. Patai and Z. Rappoport, Wiley, Chichester, 1989, ch. 13, p. 839 Search PubMed; (b) M. Abe, M. Ikeda, Y. Shirodai and M. Nojima, Tetrahedron Lett., 1996, 37, 5901 CrossRef CAS; (c) M. Abe, Y. Shirodai and M. Nojima, J. Chem. Soc., Perkin Trans. 1, 1998, 3253 RSC.
  13. S. Dayon, J. Almog, O. Khodzhaev and S. Rozen, J. Org. Chem., 1998, 63, 2752 CrossRef.
  14. M. S. Miftakhov, F. A. Akbutina, A. G. Tolstikov and A. Anpilogv, Zh. Org. Khim., 1987, 23, 2559 CAS.
  15. N. K. Base and D. N. Chandhury, J. Indian Chem. Soc., 1966, 43, 411 Search PubMed.
Click here to see how this site uses Cookies. View our privacy policy here.