Direct observation of ESR spectra of bicyclic nine-membered enediynes at ambient temperature

Masahiro Hirama, Kimio Akiyama, Parthasarathi Das, Takashi Mita, Martin J. Lear, Kyo ichiro Iida, Itaru Sato, Fumihiko Yoshimura, Toyonobu Usuki, Shozo Tero-Kubota

Research output: Contribution to journalArticlepeer-review

11 Citations (Scopus)

Abstract

The ESR spectra for synthetic bicyclo[7.3.0]epoxydodecadienediynes in solution at room temperature are steady. These spectra originate from the Masamune-Bergman cyclization of bicyclo[7.3.0]epoxydodecadienediynes to p-benzyne biradicals and the equilibrium between the two forms. Comparison of the ESR spectra of the unlabeled and 13C-labeled nine-membered enediynes indicated that the spectra are not directly due to the p-benzyne biradicals but rather to more stable secondary radical intermediates.

Original languageEnglish
Pages (from-to)83-89
Number of pages7
JournalHeterocycles
Volume69
Issue number1
DOIs
Publication statusPublished - 2006 Dec 1

ASJC Scopus subject areas

  • Analytical Chemistry
  • Pharmacology
  • Organic Chemistry

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