Unusually high ortho-selectivity in electrophilic aromatic substitution promoted by GaCl3

Fumi Yonehara, Yoshiyuki Kido, Masahiko Yamaguchi

Research output: Contribution to journalArticle

24 Citations (Scopus)

Abstract

1,4-Bis(trimethylsilyl)buta-1,3-diyne in the presence of GaCl3 reacts with aromatic hydrocarbons at -90 to -100 °C yielding 2-arylbut-1-en-3-ynes; the reactions exhibit an unusually high tendency to alkenylate the o-position of alkyl substituents; toluene, ethylbenzene and isopropylbenzene react predominantly to exclusively at the o-position while o-xylene and 1,2,3,4- tetrahydronaphthalene react at the 3 and 5-position, respectively.

Original languageEnglish
Pages (from-to)1189-1190
Number of pages2
JournalChemical Communications
Issue number13
DOIs
Publication statusPublished - 2000 Jul 7

ASJC Scopus subject areas

  • Catalysis
  • Electronic, Optical and Magnetic Materials
  • Ceramics and Composites
  • Chemistry(all)
  • Surfaces, Coatings and Films
  • Metals and Alloys
  • Materials Chemistry

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