Thermal metal-free [2+2] cycloaddition of acetylenedicarboxylates to polysubstituted butadienes

Benjamin Prek 1 , Marta Počkaj 1 , Willi Kantlehner 2 ,  and Branko Stanovnik 3 , 4
  • 1 Faculty of Chemistry and Chemical Technology, University of Ljubljana, Večna pot 113, P. O. Box 537, 1000 Ljubljana, Slovenia
  • 2 Fakultät Chemie/Organische Chemie, Hochschule Aalen, Beethovenstr. 1, 73430 Aalen, Germany
  • 3 Faculty of Chemistry and Chemical Technology, University of Ljubljana, Večna pot 113, P. O. Box 537, 1000 Ljubljana, Slovenia
  • 4 EN_FIST Centre of Excellence, Trg Osvobodilne fronte 3, 1000 Ljubljana, Slovenia
Benjamin Prek
  • Faculty of Chemistry and Chemical Technology, University of Ljubljana, Večna pot 113, P. O. Box 537, 1000 Ljubljana, Slovenia
  • Search for other articles:
  • degruyter.comGoogle Scholar
, Marta Počkaj
  • Faculty of Chemistry and Chemical Technology, University of Ljubljana, Večna pot 113, P. O. Box 537, 1000 Ljubljana, Slovenia
  • Search for other articles:
  • degruyter.comGoogle Scholar
, Willi Kantlehner
  • Fakultät Chemie/Organische Chemie, Hochschule Aalen, Beethovenstr. 1, 73430 Aalen, Germany
  • Search for other articles:
  • degruyter.comGoogle Scholar
and Branko Stanovnik
  • Corresponding author
  • Faculty of Chemistry and Chemical Technology, University of Ljubljana, Večna pot 113, P. O. Box 537, 1000 Ljubljana, Slovenia
  • EN_FIST Centre of Excellence, Trg Osvobodilne fronte 3, 1000 Ljubljana, Slovenia
  • Email
  • Search for other articles:
  • degruyter.comGoogle Scholar

Abstract

The thermal metal-free [2+2] cycloadditions of electron-poor acetylenes to some polysubstituted systems with conjugated double bonds (polysubstituted butadienes) are described.

  • [1]

    B. Stanovnik, Org. Prep. Proced. Int. 2014, 46, 24.

  • [2]

    J. Bezenšek, T. Koleša, U. Grošelj, A. Meden, K. Stare, J. Svete, B. Stanovnik, Curr. Org. Chem. 2011, 15, 2530.

    • Crossref
    • Export Citation
  • [3]

    J. Bezenšek, T. Koleša, U. Grošelj, J. Wagger, K. Stare, A. Meden, J. Svete, B. Stanovnik, Tetrahedron Lett. 2010, 51, 3392.

    • Crossref
    • Export Citation
  • [4]

    F. Bohlmann, D. Rahtz, Chem. Ber. 1957, 90, 2265.

  • [5]

    M. C. Bagley, J. W. Dale, J. Bower, Synlett 2001, 1149.

  • [6]

    J. Bezenšek, B. Prek, U. Grošelj, M. Kasunič, J. Svete, B. Stanovnik, Tetrahedron 2012, 68, 4719.

    • Crossref
    • Export Citation
  • [7]

    G. Maas, B. Singer, P. Wald, M. Gimmy, Chem. Ber. 1988 , 121, 1847.

    • Crossref
    • Export Citation
  • [8]

    R. Rahm, G. Maas, Chem. Ber. 1994 , 127, 1295.

  • [9]

    K. Drandarov, I. Tiritiris, O. Wassiljew, H.-U. Siehl, W. Kantlehner, Chem. Eur. J. 2011, 18, 7224.

  • [10]

    J. Bezenšek, B. Prek, U. Grošelj, A. Golobič, K. Stare, J. Svete, W. Kantlehner, G. Maas, B. Stanovnik, Z. Naturforsch. 2014, 69b, 554.

  • [11]

    B. Prek, J. Bezenšek, M. Kasunič, U. Grošelj, J. Svete, B. Stanovnik, Tetrahedron 2014, 70, 2359.

    • Crossref
    • Export Citation
  • [12]

    B. Prek, U. Grošelj, M. Kasunič, S. Zupančič, J. Svete, B. Stanovnik, Aust. J. Chem. 2015, 68, 184.

    • Crossref
    • Export Citation
  • [13]

    B. Prek, J. Bezenšek, B. Stanovnik, Tetrahedron 2017, 73, 5260, and references cited therein.

    • Crossref
    • Export Citation
  • [14]

    J. Bezenšek, B. Prek, U. Grošelj, M. Počkaj, J. Svete, B. Stanovnik, Tetrahedron 2015, 71, 7209.

    • Crossref
    • Export Citation
  • [15]

    J. Bezenšek, U. Grošelj, M. Počkaj, J. Svete, B. Stanovnik, Tetrahedron Lett. 2015, 56, 5705.

    • Crossref
    • Export Citation
  • [16]

    M. Kiesel, E. Haug, W. Kantlehner, J. Prakt. Chem. 1997, 339, 159–170.

    • Crossref
    • Export Citation
  • [17]

    W. Kantlehner, M. Vettel, H. Lehmann, K. Edelmann, R. Stieglitz, I. C. Ivanov, J. Prakt. Chem. 1998, 340, 408.

    • Crossref
    • Export Citation
  • [18]

    K. Edelmann, Dissertation, Universität Stuttgart, Stuttgart, 1998, p. 103.

  • [19]

    K. Edelmann, Dissertation, Universität Stuttgart, Stuttgart, 1998, p.104.

  • [20]

    W. Kantlehner, H. Lehmann, T. Stahl, W. Kaim, Chem. Ztg. 1991, 115, 183.

  • [21]

    J. Mezger, Dissertation, Universität Stuttgart, Stuttgart, 2002, p. 173.

  • [22]

    H. Lehmann, Dissertation, Universität Stuttgart, Stuttgart, 1991, p. 14.

  • [23]

    T. Sasada, F. Kobayashi, N. Sakai, T. Konakahara, Org. Lett. 2009, 11, 2161.

  • [24]

    CrysAlis Pro Software System, Intelligent Data Collection and Processing Software for Small Molecule and Protein Crystallography, Agilent Technologies Ltd., Yarnton, Oxfordshire (UK), 2011.

  • [25]

    A. Altomare, M. C. Burla, M. Camalli, G. L. Cascarano, C. Giacovazzo, A. Guagliardi, A. G. G. Moliterni, G. Polidori, R. Spagna, Sir97, A New Tool for Crystal Structure Determination and Refinement, Bari, Perugia, Rome (Italy), 1997.

  • [26]

    A. Altomare, M. C. Burla, M. Camalli, G. L. Cascarano, C. Giacovazzo, A. Guagliardi, A. G. G. Moliterni, G. Polidori, R. Spagna, J. Appl. Crystallogr. 1999, 32, 115.

    • Crossref
    • Export Citation
  • [27]

    L. J. Bourhis, O. V. Dolomanov, R. J. Gildea, J. A. K. Howard, H. Puschmann, Acta Crystallogr. 2015, A71, 59.

  • [28]

    G. M. Sheldrick, Shelxl-2014/7, Program for the Refinement of Crystal Structures, University of Göttingen, Göttingen (Germany), 2013.

  • [29]

    G. M. Sheldrick, Acta Crystallogr. 2015, C71, 3.

  • [30]

    C. K. Johnson, M. N. Burnett, Ortep-III (version 1.0.2), Oak Ridge Thermal Ellipsoid Plot Program for Crystal Structure Illustrations, Rep. ORNL-6895, Oak Ridge National Laboratory, Oak Ridge, TN (USA), 1996.

  • [31]

    Windows version: L. J. Farrugia, University of Glasgow, Glasgow, Scotland (UK), 1999.

  • [32]

    L. J. Farrugia, J. Appl. Crystallogr. 2012, 45, 849.

Purchase article
Get instant unlimited access to the article.
€30.00
Log in
Already have access? Please log in.


or
Log in with your institution

Journal + Issues

Zeitschrift für Naturforschung B is an international scientific journal which publishes original papers, microreviews, and letters from all areas of inorganic chemistry, solid state chemistry, coordination chemistry, molecular chemistry, and organic chemistry.

Search