Novel Photoreactions of Benzhydrylidenequadricyclane and Quadricyclanone: A New Route to Trimethylenemethane and Oxyallyl Derivatives

Takashi Hirano, Tsutomu Kumagai, Tsutomu Miyashi, Kimio Akiyama, Yusaku Ikegami

Research output: Contribution to journalArticlepeer-review

37 Citations (Scopus)

Abstract

The irradiation of 3-benzhydrylidenequadricyclane (1) generated a trimethylenemethane (TMM) derivative, 3-benzhydrylidenebicyclo[3.2.0]hept-6-ene-2,4-diyl (3), which dimerized and could be chemically captured by molecular oxygen and acrylonitrile, but not by furan, methanol, or ethyl vinyl ether. The triplet nature of 3 was confirmed by EPR, emission, and absorption spectra. By contrast, the irradiation of quadricyclanone (2) generated the singlet oxyallyl (OA), 3-oxobicyclo[3.2.0]hept-6-ene-2,4-diyl (4), which could be captured by furan, methanol, and ethyl vinyl ether, but not by molecular oxygen or acrylonitrile, indicating the zwitterionic and electron-accepting nature of 4.

Original languageEnglish
Pages (from-to)1907-1914
Number of pages8
JournalJournal of Organic Chemistry
Volume56
Issue number5
DOIs
Publication statusPublished - 1991 Mar 1

ASJC Scopus subject areas

  • Organic Chemistry

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