Rearrangement of a 2-Methylenecyclobutanone Derivative Triggered by Photoinduced Electron Transfer: An Unprecedented Oxa Analogue of the Tetramethyleneethane Radical Cation

Hiroshi Ikeda, Futoshi Tanaka, Kimio Akiyama, Shozo Tero-Kubota, Tsutomu Miyashi

Research output: Contribution to journalArticlepeer-review

17 Citations (Scopus)

Abstract

On irradiation of p-chloranil (CA), 2,2-bis(p-methoxyphenyl)-3,3-dimethyl-4-methylenecyclobutanone (1) gives 2,2-bis(p-methoxyphenyl)-4-isopropylidenecyclobutanone (2), whereas 2 affords a CA adduct (4), suggesting that a novel rearrangement of 1 to give 2 occurs irreversibly via intermediate 3•+, a radical cation variant of an unprecedented oxa analogue of tetramethyleneethane.

Original languageEnglish
Pages (from-to)414-415
Number of pages2
JournalJournal of the American Chemical Society
Volume126
Issue number2
DOIs
Publication statusPublished - 2004 Jan 21

ASJC Scopus subject areas

  • Catalysis
  • Chemistry(all)
  • Biochemistry
  • Colloid and Surface Chemistry

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