Effect of aryl substituents on intramolecular cyclization of 2,2′-biphenoquinones

Naoto Hayashi, Akifumi Kanda, Taku Kamoto, Hiroyuki Higuchi, Takeyuki Akita

Research output: Contribution to journalArticlepeer-review

3 Citations (Scopus)


Effect of aryl substituents on intramolecular cyclizations of 3,3′,5,5′-tetraaryl-2,2′-biphenoquinones (Ar = phenyl (la) and 4-methoxyphenyl (1b)) has been studied. In benzene, 1a gave 2,4,6,8-tetraphenyldibenzofuran-1-ol (10) gradually as a main product, indicating the phenyl substituents preferred to stabilize the intermediate by derealization of the negative charge rather than that of the positive one. In contrast, the reaction of 1b occurred spontaneously in order to give a complex mixture, which should be due to 4-methoxyphenyl substituent at the 3 position.

Original languageEnglish
Pages (from-to)865-872
Number of pages8
Issue numberC
Publication statusPublished - 2009

All Science Journal Classification (ASJC) codes

  • Analytical Chemistry
  • Pharmacology
  • Organic Chemistry


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