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Characterization of tetraene intermediates formed in the [3+2]-photocycloaddition of 1,4-dicyano-6-methylnaphthalene with styrene

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Abstract

The early stages of the [3+2]-photocycloaddition of 1,4-dicyano-6-methylnaphthalene (6) with styrene (7) were investigated by UV–visible absorption and 1H NMR spectroscopy. An intermediate species was detected and characterized as 8-methyl-2-phenyl-1,2,2a,8-tetrahydroacenaphthylene-2a,5-dicarbonitrile (9). Computational studies explained the regioselective [3+2]-photocycloaddition at the 4,5-position of 6 to form zwitterion 8, and subsequent thermal transformation to form 9.

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Authors and Affiliations

  1. Department of Materials Science, Faculty of Science and Engineering, Shimane University, 1060 Nishikawatsu, Matsue, Shimane, 690-8504, Japan

    Hideo Shiratori, Yuki Nogami & Yasuo Kubo

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  1. Hideo Shiratori
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  2. Yuki Nogami
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  3. Yasuo Kubo
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Correspondence to Hideo Shiratori or Yasuo Kubo.

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Shiratori, H., Nogami, Y. & Kubo, Y. Characterization of tetraene intermediates formed in the [3+2]-photocycloaddition of 1,4-dicyano-6-methylnaphthalene with styrene. Res Chem Intermed 39, 49–59 (2013). https://doi.org/10.1007/s11164-012-0631-9

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  • DOI: https://doi.org/10.1007/s11164-012-0631-9

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