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Synthesis of cycloalkynes via photochemical decarboxylation of ω-phthalimidoalkynoates

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Abstract

The photodecarboxylation reactions of ω-phthalimidoalkynoates have been studied and the influence of the geometrically restricted acetylene linker on the photocyclization efficiency investigated. Less flexible starting materials give solely CO2H/H-exchange products in good yields. In contrast, derivatives with appropriate chain lengths give the corresponding macrocycles in fair to moderate isolated yields. Furthermore, photodecarboxylative addition of alkynoates to N-methylphthalimide gives hydroxyphthalimidines in acceptable yields.

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Authors and Affiliations

  1. Department of Chemistry, Seonam University, 720 Gwangchi-Dong, Namwon-Si, Chonbuk, 590-711, Korea

    Dong Jin Yoo

  2. Center for Molecular Design and Synthesis, Department of Chemistry and School of Molecular Science (BK21), Korea Advanced Institute of Science and Technology, 373-1 Guseong-Dong, Yuseong-Gu, Daejon, 305-701, Korea

    Eun Young Kim & Sang Chul Shim

  3. Bayer CropScience K.K., 9511-4 Yuki, Yuki-City, Ibaraki, 307-0001, Japan

    Michael Oelgemöller

Authors
  1. Dong Jin Yoo
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  2. Eun Young Kim
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  3. Michael Oelgemöller
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  4. Sang Chul Shim
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Corresponding authors

Correspondence to Dong Jin Yoo or Michael Oelgemöller.

Additional information

This paper is dedicated to the memory of Professor Sang Chul Shim (KAIST), deceased April 10th, 2002.

Electronic supplementary information (ESI) available: 1H- and 13C-NMR spectra for compounds 5a, b, 6, 7a–c and 10a–d. See http://www.rsc.org/suppdata/pp/b3/b312263h/

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Yoo, D.J., Kim, E.Y., Oelgemöller, M. et al. Synthesis of cycloalkynes via photochemical decarboxylation of ω-phthalimidoalkynoates. Photochem Photobiol Sci 3, 311–316 (2004). https://doi.org/10.1039/b312263h

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  • DOI: https://doi.org/10.1039/b312263h

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