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Synthesis 2003(7): 1043-1048
DOI: 10.1055/s-2003-39160
PAPER
© Georg Thieme Verlag Stuttgart ˙ New York

Rearrangement of Allyl Aryl Ethers; VI: [1] Reaction of Naphthols with Cycloalkadienes

Olivér Orovecza, Péter Kovácsc, Pál Kolonitsa, Zoltán Kaletaa, László Párkányic, Éva Szabód, Lajos Novák*a,b
a Institute for Organic Chemistry, Budapest University of Technology and Economics, 1111, Budapest, Szt. Gellért tér 4, Hungary
Fax: +36(1)4633297; e-Mail: lnovak@mail.bme.hu;
b Research Group for Alkaloid Chemistry, Hungarian Academy of Sciences, 1111, Budapest, Szt. Gellért tér 4, Hungary
c Central Research Institute of Chemistry, 1525, Budapest, P.O. Box 17, Hungary
d EGIS Pharmaceuticals LTD, 1475, Budapest 10, P.O. Box 100, Hungary
Further Information

Publication History

Received 14 February 2003
Publication Date:
09 May 2003 (online)

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Abstract

Cycloalkanonaphthofurans 5, 6, and 10 were prepared in one pot reaction from naphthols 1 and 7 with cycloalka-1,3-dienes 2. The mechanism of these novel reactions is also discussed.

Key words

rearrangemenst - furans - 1-naphthol - 2-naphthol - cycloalka-1,3-dienes - ethers

    References

  • 1 For Part V, see: Orovecz O. Kovács P. Kolonits P. Párkányi L. Szabó . Novák L. Synthesis  2002,  2711 
    Thieme Connect
  • 2 Novák L. Kovács P. Kolonits P. Orovecz O. Fekete J. Szántay C. Synthesis  2000,  809 
    Thieme Connect
  • 4 Wilkinson G. Org. Synth., Coll. Vol. 4   Wiley; New York: 1963.  p.476 
  • 5 Sheldrick GM. SHELXS-97 Program for Crystal Structure Solution   University of Göttingen; Germany: 1997. 
  • 6 Sheldrick GM. SHELXS-97 Program for Crystal Structure Refinement   University of Göttingen; Germany: 1997. 
3

Besides the major product we isolated small amounts of 1-(naphthalen-2-yloxy)-2,3,3a,4,7,7a-hexahydro-1H-4,7-methanoindene.