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Photochemical reactions of 1,2-diketones with silyl enol ethers

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Abstract

Results arising from the current study demonstrate that UV irradiation-induced photoaddition reactions of the 1,2-diketones, acenaphthenequinone, 9,10-phenanthrenequinone, and benzil, with silyl enol ethers derived from propionaldehyde and isobutyraldehyde take place to form a variety of adducts. Product formation in these cases takes place mainly via two mechanistic pathways, one initiated by single electron transfer (SET) and the other by [2 + 2]-cycloaddition. In addition, observations show that the competition between these pathways depends on the nature of the substrates. An exploration of the photoreactions of acenaphthenequinone revealed that photoinduced SET is the predominant process occurring when the dimethyl-substituted silyl enol ether serves as a reactant, while cycloaddition and other excited state reactions become competitive with SET when the mono-methyl substituted silyl enol ether is used as a substrate. In the case of 9,10-phenanthrenequinone, photoreactions take place by [4 + 2]-cycloaddition routes regardless of the nature of the silyl enol ether employed. Finally, irradiation of benzil in the presence of both silyl enol ethers leads to exclusive or predominant formation of products arising by [2 + 2]-cycloaddition and photoinduced benzoyl radical forming α-cleavage.

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Acknowledgments

This study was supported by a 2011 Yeungnam University Research Grant (211A054013 for D.W. Cho) and National Research Foundation of Korea Grant funded by the Korean Government (2012R1A1A2007158 for U.C. Yoon).

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Authors and Affiliations

  1. Department of Chemistry and Chemistry Institute for Functional Materials, Pusan National University, Busan, 609-735, South Korea

    Hea Jung Park & Ung Chan Yoon

  2. Analysis Research Division, Daegu Center, Korea Basic Science Institute, Daegu, 702-701, South Korea

    Sung Hong Kim

  3. Department of Chemistry, Yeungnam University, Gyeongsan, Gyeongbuk, 712-749, South Korea

    Youngku Sohn & Dae Won Cho

  4. Department of Chemistry and Chemical Biology, University of New Mexico, Albuquerque, NM, 87131, USA

    Patrick S. Mariano

Authors
  1. Hea Jung Park
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  2. Ung Chan Yoon
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  5. Dae Won Cho
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Correspondence to Ung Chan Yoon or Dae Won Cho.

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Park, H.J., Yoon, U.C., Kim, S.H. et al. Photochemical reactions of 1,2-diketones with silyl enol ethers. Res Chem Intermed 41, 419–431 (2015). https://doi.org/10.1007/s11164-013-1203-3

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