Synthesis of some new enantiopure [2.2]paracyclophanes bearing polycyclic aromatic subunits

Daniela Lanari, Assunta Marrocchi, Lucio Minuti, Aldo Taticchi, Eszter Gacs-Baitz

Research output: Contribution to journalArticle

16 Citations (Scopus)

Abstract

The synthesis of some new optically active[2.2]paracyclophanes containing condensed polycyclic aromatic subunits is described. The Diels-Alder reactions of (S)-(+)-4-ethenyl[2.2]paracyclophane with 1,4-naphthoquinone, 5-hydroxy-1,4-naphthoquinone and 5,8-dihydroxy-1,4-naphthoquinone have been studied. The effect of the hydroxy group(s) on the reactivity of the dienophiles and on the regioselectivity of the Diels-Alder reaction has been discussed. A structural analysis of the reaction products by 1H and 13C NMR spectroscopy is also presented.

Original languageEnglish
Pages (from-to)1331-1335
Number of pages5
JournalTetrahedron Asymmetry
Volume13
Issue number12
DOIs
Publication statusPublished - Jul 5 2002

ASJC Scopus subject areas

  • Catalysis
  • Physical and Theoretical Chemistry
  • Organic Chemistry
  • Inorganic Chemistry

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