Cycloaddition reactions of 1,4-dihydronaphthalene-1,4-epoxide with cyclohexadiene and 7-(methoxycarbonyl)cycloheptatriene: Selectivity in additions


MENZEK A., ALTUNDAS A., CORUH U., AKBULUT N., LOPEZ E., Hokelek T., ...More

EUROPEAN JOURNAL OF ORGANIC CHEMISTRY, no.5, pp.1143-1148, 2004 (Peer-Reviewed Journal) identifier identifier

  • Publication Type: Article / Article
  • Publication Date: 2004
  • Doi Number: 10.1002/ejoc.200300569
  • Journal Name: EUROPEAN JOURNAL OF ORGANIC CHEMISTRY
  • Journal Indexes: Science Citation Index Expanded, Scopus
  • Page Numbers: pp.1143-1148
  • Keywords: alcohols, bromination, cycloaddition, halogenation, HIGH-TEMPERATURE BROMINATION, 1,3-DIPOLAR CYCLO-ADDITIONS, BENZHOMOBARRELENE DERIVATIVES, REARRANGEMENT REACTIONS, CONTAINING HETEROCYCLES, DOUBLE-BOND, 1,4-EPOXY-1,4-DIHYDRONAPHTHALENE, BEHAVIOR, ADDUCTS, SPECTRA

Abstract

Cycloaddition reactions of naphthalene-1,4-epoxide (1) with both 7-(methoxycarbonyl)cycloheptatriene (2) and cyclohexadiene (4) give adducts of type 3 and 5 exclusively. Selectivity was observed for the cycloaddition and bromination reactions, but neighboring group participation also occurrs in the latter. The formation of the products is discussed. (C) Wiley-VCH Verlag GmbH & Co. KGaA, 69451 Weinheim, Germany, 2004.