Photocyclization of a conformationally constrained 2-vinylbiphenyl

Meledathu C. Sajimon, Frederick D Lewis*

*Corresponding author for this work

Research output: Contribution to journalArticlepeer-review

8 Scopus citations

Abstract

The synthesis and photochemical behavior of a rigid analog of syn-2-vinylbiphenyl are reported. This analog undergoes quantitative conversion to a tetrahydrobenzanthracene derivative upon irradiation in fluid solution. Product formation is proposed to occur via photocyclization to yield an unstable intermediate followed by an intramolecular thermal hydrogen shift. The intermediate can be observed upon irradiation at low temperature either in a rigid glass or in liquid propane solution. The temperature dependence of its decay is indicative of a tunneling mechanism for the hydrogen shift process.

Original languageEnglish (US)
Pages (from-to)789-791
Number of pages3
JournalPhotochemical and Photobiological Sciences
Volume4
Issue number10
DOIs
StatePublished - Oct 1 2005

ASJC Scopus subject areas

  • Physical and Theoretical Chemistry

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