High pressure and thermal Diels-Alder reactions of 5-nitro[2.2]paracyclophanepyran-6-one

Lucio Minuti, Assunta Marrocchi, Selvaggia Landi, Mirko Seri, Eszter Gacs-Baitz

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13 Citations (Scopus)

Abstract

The Diels-Alder reactions of 5-nitro[2.2]paracyclophanepyran-6-one with 1,3-butadienes and 1,2-dihydro-3-vinyl-naphthalene were examined under thermal and high-pressure conditions. The cycloadditions with 1,3-butadienes occurred in good yield and anti-exo diastereoselectively only under high-pressure conditions; the one with 1,2-dihydro-3-vinyl-naphthalene afforded comparable yields of mixtures of anti/syn adducts under normal and high-pressure conditions. A structural analysis of the reaction products by 1H and 13C NMR spectroscopy is presented.

Original languageEnglish
Pages (from-to)5477-5481
Number of pages5
JournalTetrahedron
Volume63
Issue number25
DOIs
Publication statusPublished - Jun 18 2007

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Keywords

  • Coumarins
  • Diels-Alder cycloaddition
  • High pressure
  • [2.2]Paracyclophanes

ASJC Scopus subject areas

  • Biochemistry
  • Drug Discovery
  • Organic Chemistry

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