Stable endoperoxide of 4,5,6,8,16-pentamethyl[2.2]metacyclophane; structural analysis and deoxygenation

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

Tsuyoshi Sawada, Keisuke Mimura, Thies Thiemann, Takehiko Yamato, Masashi Tashiro and Shuntaro Mataka


Abstract

Photooxygenation of 4,5,6,8,16-pentamethyl[2.2]metacyclophane 6 gives [2.2]metacyclophane endoperoxide 7; its X-ray crystallographic analysis and stability in the thermal deoxygenation reaction are reported.


References

  1. (a) A. Izuoka, T. Murase, M. Tsukada, Y. Ito, T. Sugawara, A. Uchida, N. Sato and H. Inokuchi, Tetrahedron Lett., 1997, 38, 245 CrossRef CAS; (b) M. Balci, Chem. Rev., 1981, 81, 91 CrossRef CAS; (c) H. H. Wassermann and R. W. Murray, Singlet Oxygen, Academic Press, New York, 1979 Search PubMed.
  2. R. Gray and V. Boekelheide, J. Am. Chem. Soc., 1979, 101, 2128 CrossRef CAS.
  3. (a) M. Stöbbe, S. Kirchmeyer, G. Adiwidjaja and A. de Meijere, Angew. Chem., 1986, 98, 739; Angew. Chem., Int. Ed. Engl., 1986, 25, 171 Search PubMed; (b) I. Erden, P. Gölitz, R. Näder and A. de Meijere, Angew. Chem., 1981, 93, 605 CAS; Angew. Chem., Int. Ed. Engl., 1981, 20, 583 Search PubMed.
  4. (a) G. W. Wijsman, D. S. van Es, W. H. de Wolf and F. Bickelhaupt, Angew Chem., 1993, 105, 739 CAS; Angew. Chem., Int. Ed. Engl., 1993, 32, 726; during our investigation, an endoperoxide of [2.2]metacyclophane-1,9-diene was reported Search PubMed; (b) H. Cerfontain, A. Koeberg-Telder, B. H. Bakker, R. H. Mitchell and M. Tashiro, Liebigs Ann., 1997, 873 Search PubMed.
  5. M. Tashiro, T. Yamato, K. Kobayashi and T. Arimura, J. Org. Chem., 1987, 52, 3196 CrossRef CAS.
  6. (a) C. J. M. van den Heuvel, H. Steinberg and Th. J. de Boer, Recl. Trav. Chim. Pays-Bas, 1980, 99, 275 CAS; (b) C. J. M. van den Heuvel, H. Steinberg and Th. J. de Boer, Recl. Trav. Chim. Pays-Bas, 1977, 97, 157.
  7. N. J. Turro, M. Chow and J. Rigaudy, J. Am. Chem. Soc., 1981, 103, 7218 CrossRef CAS.
  8. (a) C. L. Klein, F. D. Stevens, D. E. Zacharias and D. P. Glusker, Carcinogenesis, 1987, 8, 5 CAS; (b) Y. Kobayashi, S. Mochizuki, H. Yoshioka, K. Nakatsu, T. Arai, T. Ishii and S. Tokita, Proc. 2nd Int. Symp. on Chem. of Functional Dyes, 1993, 425 Search PubMed; (c) D. J. Coughlin, R. S. Brown and R. G. Salomon, J. Am. Chem. Soc., 1979, 101, 1533 CrossRef CAS.
  9. A. Altomare, M. C. Burla, M. Camalli, G. Cascarano, C. Giacovazzo, A. Guagliardi and G. Polidori, J. Appl. Crystallogr., 1994, 27, 435 CrossRef.
  10. MolEN, An Interactive Structure Solution Procedure, Enraf-Nonius, Delft, The Netherlands, 1990.
  11. SHELXL-93, G. M. Sheldrick, University of Göttingen, Germany, 1993.
Click here to see how this site uses Cookies. View our privacy policy here.