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Photocyclization of a conformationally constrained 2-vinylbiphenyl

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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.

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Authors and Affiliations

  1. Department of Chemistry, Northwestern University, Evanston, Illinois, 60208-3113, USA

    Meledathu C. Sajimon & Frederick D. Lewis

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  1. Meledathu C. Sajimon
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  2. Frederick D. Lewis
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Correspondence to Frederick D. Lewis.

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Sajimon, M.C., Lewis, F.D. Photocyclization of a conformationally constrained 2-vinylbiphenyl. Photochem Photobiol Sci 4, 789–791 (2005). https://doi.org/10.1039/b511270b

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