View PDF Version
 
DOI: 10.1039/A702108I (Paper) Reference Section for: J. Chem. Soc., Perkin Trans. 1, 1997, 2879-2890

Furan-2(3H)- and -2(5H)-ones. Part 8.1 Conformation and di-π-methane reactivity of the 4,7-disubstituted tetrahydroisobenzofuran-1-one system: a mechanistic and exploratory study

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

Osamu Muraoka, Genzoh Tanabe, Emi Yamamoto, Masaru Ono, Toshie Minematsu and Takayoshi Kimura

Abstract

Photoirradiation of cis- and trans-4,7-diphenyl-1,3,4,7-tetrahydroisobenzofuran-1-one cis- and trans-14 and its 4-methyl analogues cis- and trans-15 afford the corresponding di-π-methane rearrangement products 27, 28 and 24 in moderate yields. MM2 calculations for the cis- and trans-4,7-diphenyl substrates cis- and trans-14 showed that the planar structure is most stable for both compounds and that the molecular energy difference between the planar structure and the boat conformation is small enough for a boat–planar–boat conversion. On the basis of the calculations, the di-π-methane rearrangement of the compounds 14 and 15 is supposed to proceed via the boat conformation with a pseudoaxial phenyl substituent. An X-ray structure determination of the two diphenyl substrates cis- and trans-14 provides strong support for the validity of the calculations in predicting optimum structures for cis- and trans-disubstituted tetrahydroisobenzofuranone.

References

  1. Part 7, O. Muraoka, G. Tanaba and Y. Igaki, J. Chem. Soc., Perkin Trans. 1, 1997, 1669 Search PubMed.
  2. T. Momose, K. Kanai and T. Nakamura, Chem. Pharm. Bull., 1978, 26, 1592 CAS; Heterocycles, 1976, 4, 1481 Search PubMed.
  3. T. Momose, G. Tanabe, H. Tsujimori and O. Muraoka, Chem. Pharm. Bull., 1992, 40, 2525 CAS; T. Momose, G. Tanabe, H. Tsujimori, M. Higashiura, I. Imanishi and K. Kanai, Heterocycles, 1989, 29, 257 CAS.
  4. O. Muraoka, G. Tanabe, K. Sano, T. Minematsu and T. Momose, J. Chem. Soc., Perkin Trans. 1, 1994, 1833 RSC; O. Muraoka, G. Tanabe, K. Sano and T. Momose, Heterocycles, 1992, 34, 1093 CAS.
  5. O. Muraoka, G. Tanabe, K. Sano, T. Minematsu and T. Momose, J. Chem. Soc., Perkin Trans. 1, 1995, 1437 RSC; O. Muraoka, G. Tanabe and T. Momose, Heterocycles, 1990, 31, 1589 CAS.
  6. K. Friedrich and H.-G. Henning, Chem. Ber., 1959, 92, 2944 CAS.
  7. L. F. Fieser and M. J. Haddadin, J. Am. Chem. Soc., 1964, 86, 2392 CrossRef CAS.
  8. A. Numata, K. Ohno, H. Irie and S. Uyeo, Yakugaku Zasshi, 1968, 88, 1151 (Chem. Abstr, 1969, 70, 47 193a) Search PubMed.
  9. M. Schlosser and K. F. Christmann, Liebigs Ann. Chem., 1967, 708, 1 Search PubMed.
  10. D. G. Morris, in The Chemistry of the Cyclopropyl Group, ed. Z. Rappoport, John Wiley and Sons, New York, 1987, Part 1, p. 101 Search PubMed.
  11. (a) R. K. Dhar, A. Sygula, F. R. Fronczek and P. W. Rabideau, Tetrahedron, 1992, 48, 9417 CrossRef CAS; (b) P. W. Rabideau, J. L. Mooney and K. B. Lipkowitz, J. Am. Chem. Soc., 1986, 108, 8130 CrossRef CAS; (c) P. W. Rabideau, K. B. Lipkowitz and R. B. Nachbar Jr., J. Am. Chem. Soc., 1984, 106, 3119 CrossRef CAS; (d) P. W. Rabideau and D. M. Wetzel, J. Org. Chem., 1982, 47, 3993 CrossRef CAS; (e) K. B. Lipkowitz, P. W. Rabideau, D. J. Raber, L. E. Hardee, P. v. R. Schleyer, A. J. Kos and R. A. Kahn, J. Org. Chem., 1982, 47, 1002 CrossRef CAS; (f) P. W. Rabideau, Acc. Chem. Res., 1978, 11, 141 CrossRef CAS; (g) W. B. Smith and B. A. Shoulders, J. Phys. Chem., 1965, 69, 2022 CAS and references cited therein.
  12. C. J. Gilmore, J. Appl. Crystallogr., 1984, 17, 42 CrossRef CAS.
  13. TEXSAN: TEXRAY Structure Analysis Package, Molecular Structures Corporation, The Woodland, Texas, 1985.
Click here to see how this site uses Cookies. View our privacy policy here.