View PDF Version
 
DOI: 10.1039/A700605E (Paper) Reference Section for: J. Chem. Soc., Perkin Trans. 2, 1997, 2095-2098

New one-pot synthesis of a benzonorcaradiene derivative by reduction of naphthalic anhydride with LiAlH4

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

Geerlig W. Wijsman, Lars A. van der Veen, Willem H. de Wolf and Friedrich Bickelhaupt

Abstract

Reaction of naphthalic anhydride (naphthalene-1,8-dicarboxylic anhydride) (1) or of 1,8-bis(hydroxymethyl)naphthalene (3) with LiAlH4 in refluxing THF yields the benzonorcaradiene derivatives 2 in yields of up to 50%. It is proposed that in the formation of this (strained) product an anti-hydroalumination reaction is involved, which is facilitated by the assistance of a neighbouring alkoxide function.

References

  1. (a) F. Bickelhaupt and W. H. de Wolf, in Advances in Strain in Organic Chemistry, ed. B. Halton, JAI Press, London, 1993, vol. 3, pp. 185–227 and references cited therein Search PubMed; (b) F. Bickelhaupt and W. H. de Wolf, Recl. Trav. Chim. Pays-Bas, 1988, 107, 459 CAS; (c) 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 Search PubMed.
  2. (a) R. E. Beyler and L. H. Sarett, J. Am. Chem. Soc., 1952, 74, 1406 CrossRef CAS; (b) V. Boekelheide and G. K. Vick, J. Am. Chem. Soc., 1956, 78, 653 CrossRef CAS; (c) R. H. Mitchell and F. Sondheimer, Tetrahedron, 1968, 24, 1397 CrossRef CAS.
  3. (a) M. Pomerantz and G. W. Gruber, J. Am. Chem. Soc., 1967, 89, 6798, 6799; (b) K. A. Burdett, F. L. Shenton, D. H. Yates and J. S. Swenton, Tetrahedron, 1974, 30, 2057 CrossRef CAS; (c) P. Wan, D. Budac, M. Earle and D. Shukla, J. Am. Chem. Soc., 1990, 112, 8048 CrossRef CAS.
  4. (a) P. Müller, G. Bernardinelli and H. C. Godoy-Nguyen Thi, Helv. Chim. Acta, 1989, 72, 1627 CrossRef; (b) M. Cristl, R. Stangl and H. Jelinek-Fink, Chem. Ber., 1992, 125, 485.
  5. (a) E. I. Snyder, J. Org. Chem., 1967, 32, 3531 CrossRef CAS; (b) F. A. Hochstein and W. G. Brown, J. Am. Chem. Soc., 1948, 70, 3484 CAS.
  6. M. J. Jorgenson and A. W. Friend, J. Am. Chem. Soc., 1965, 87, 1815 CrossRef CAS.
  7. R. T. Uyeda and D. J. Cram, J. Org. Chem., 1965, 30, 2083 CAS.
  8. L. H. Klemm, D. Hsu Lee, P. S. Santhanam, D. V. White, J. Shabtai and D. R. Olson, J. Org. Chem., 1972, 37, 2043 CrossRef CAS.
  9. W. Thatcher Borden, J. Am. Chem. Soc., 1970, 92, 4898 CrossRef CAS.
  10. R. B. Gammill, P. M. Gold and S. A. Mizsak, J. Am. Chem. Soc., 1980, 102, 3095 CrossRef CAS.
  11. M. J. Jorgenson and A. F. Thacher, J. Chem. Soc., 1969, 21D, 1290 Search PubMed.
  12. Obtained from Group Increments, S. W. Benson, Thermochemical Kinetics, Wiley, New York, 1968 Search PubMed.
Click here to see how this site uses Cookies. View our privacy policy here.