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 journalArticle

3 Citations (Scopus)

Abstract

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
JournalHeterocycles
Volume79
Issue numberC
DOIs
Publication statusPublished - Jul 29 2009

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Depersonalization
Cyclization
Benzene
Complex Mixtures

All Science Journal Classification (ASJC) codes

  • Analytical Chemistry
  • Pharmacology
  • Organic Chemistry

Cite this

Effect of aryl substituents on intramolecular cyclization of 2,2′-biphenoquinones. / Hayashi, Naoto; Kanda, Akifumi; Kamoto, Taku; Higuchi, Hiroyuki; Akita, Takeyuki.

In: Heterocycles, Vol. 79, No. C, 29.07.2009, p. 865-872.

Research output: Contribution to journalArticle

Hayashi, Naoto ; Kanda, Akifumi ; Kamoto, Taku ; Higuchi, Hiroyuki ; Akita, Takeyuki. / Effect of aryl substituents on intramolecular cyclization of 2,2′-biphenoquinones. In: Heterocycles. 2009 ; Vol. 79, No. C. pp. 865-872.
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