Short synthetic approach to benzo[g]cyclopenta[a]-phenanthrenes and benzo[g]-indeno[a]phenanthrenones

Eszter Gacs-Baitz, Lucio Minuti, Aldo Taticchi

Research output: Contribution to journalArticle

13 Citations (Scopus)

Abstract

The synthesis of 3-vinyl-phenanthrene and 4-vinyl-1, 2-dihydro-phenanthrene is reported. High pressure Lewis acid-catalyzed cycloaddition reactions of both dienes with 4-acetoxy-2-cyclopenten-1-one are discussed. Whereas 4-vinyl-1, 2-dihydro-phenanthrene underwent the expected Diels-Alder reaction, 3-vinyl-phenanthrene underwent a [2π + 2π] cycloaddition. Both cycloadditions are totally regioselective. Structure analysis of the reaction products by 1H and 13C NMR spectroscopy is reported.

Original languageEnglish
Pages (from-to)213-227
Number of pages15
JournalPolycyclic Aromatic Compounds
Volume8
Issue number4
DOIs
Publication statusPublished - Jan 1 1996

Keywords

  • Benzo[g]cyclopenta[a]phenanthrenes
  • Benzo[g]indeno[a]phenanthrenones
  • Synthesis

ASJC Scopus subject areas

  • Polymers and Plastics
  • Organic Chemistry
  • Materials Chemistry

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