Preparation of 3-(9-Anthryl)acrylates and 9-Aroylethenylanthracenes as Pi-Extended Anthracenes and Their Diels–Alder Type Adducts with Electron-Poor Dienophiles

Hasnaa Sadeq, Thies Thiemann, John Patrick Graham, Yosef al Jasem, Bernhard Bugenhagen, Nathir Ahmad Al Rawashdeh, Mazen al Sulaibi

Research output: Contribution to journalArticlepeer-review

2 Citations (Scopus)

Abstract

(E)-3-(9-Anthryl)acrylates and (E)-9-aroylethenylanthracenes have been prepared by solventless Wittig olefination with conjugated phosphoranes. The (E)-3-(9-anthryl)acrylates were brominated to give (E)-3[10-{9-bromoanthryl}]acrylates, which could be subjected to Suzuki reactions with arylboronic acids to produce (E)-3-[10-{9-arylanthryl}]acrylates as pi-extended systems. The compounds thus prepared were subjected to Diels–Alder reactions, partly under solventless conditions.

Original languageEnglish
Pages (from-to)148-160
Number of pages13
JournalPolycyclic Aromatic Compounds
Volume37
Issue number2-3
DOIs
Publication statusPublished - May 27 2017

Keywords

  • Anthracenes
  • Suzuki–Miyaura cross-coupling
  • pi-extended systems
  • solventless Diels–Alder reaction
  • solventless Wittig olefination

ASJC Scopus subject areas

  • Materials Chemistry
  • Polymers and Plastics
  • Organic Chemistry

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