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

E. Gács-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
Publication statusPublished - 1996

Fingerprint

Phenanthrenes
Cycloaddition
Lewis Acids
Reaction products
Nuclear magnetic resonance spectroscopy
Acids
1,2-dihydrophenanthrene
phenanthrene

Keywords

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

ASJC Scopus subject areas

  • Organic Chemistry

Cite this

Short synthetic approach to benzo[g]cyclopenta[a]-phenanthrenes and benzo[g]-indeno[a]phenanthrenones. / Gács-Baitz, E.; Minuti, Lucio; Taticchi, Aldo.

In: Polycyclic Aromatic Compounds, Vol. 8, No. 4, 1996, p. 213-227.

Research output: Contribution to journalArticle

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