Concise synthesis of halogenated chrysenes ([4]phenacenes) that favor π-stack packing in single crystals

Hiroyuki Lsobe, Shunpei Hitosugi, Taisuke Matsuno, Takeaki Iwamoto, Junji Ichikawa

Research output: Contribution to journalArticlepeer-review

31 Citations (Scopus)

Abstract

A concise synthesis of halogenated chrysene derivatives from 2,2,2-trifluoroethyl tosylate and halostyrene was established. Friedel-Crafts type cyclization of a 1,1 -difluoro-1 -alkene bearing halogenated phenyl moieties involved skeletal rearrangement and dehydrogenation to afford the title compound in good to moderate yield. X-ray analysis revealed that the halogen substituents induce π-stack packing of the molecules in the crystals.

Original languageEnglish
Pages (from-to)4026-4028
Number of pages3
JournalOrganic letters
Volume11
Issue number17
DOIs
Publication statusPublished - 2009 Sep 3

ASJC Scopus subject areas

  • Biochemistry
  • Physical and Theoretical Chemistry
  • Organic Chemistry

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