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Paracyclophanes: Extending the Bridges. Synthesis†

  1. Zissis Pechlivanidis1,
  2. Henning Hopf1,
  3. Ludger Ernst2

Article first published online: 25 NOV 2008

DOI: 10.1002/ejoc.200800494

Issue

European Journal of Organic Chemistry

European Journal of Organic Chemistry

Volume 2009, Issue 2, pages 223–237, January 2009

Additional Information

How to Cite

Pechlivanidis, Z., Hopf, H. and Ernst, L. (2009), Paracyclophanes: Extending the Bridges. Synthesis. Eur. J. Org. Chem., 2009: 223–237. doi: 10.1002/ejoc.200800494

Author Information

  1. 1

    Institut für Organische Chemie, Technische Universität Braunschweig, Hagenring 30, 38106 Braunschweig, Germany, Fax: +49-531-391-5388

  2. 2

    NMR-Laboratorium der Chemischen Institute der Technischen Universität Braunschweig, Hagenring 30, 38106 Braunschweig, Germany, Fax: +49-531-391-8192

  1. †

    Cyclophanes, LXII. Part LXI: Ref.‡

Publication History

  1. Issue published online: 2 JAN 2009
  2. Article first published online: 25 NOV 2008
  3. Manuscript Received: 20 MAY 2008

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Keywords:

  • Cyclophanes;
  • Thiacyclophanes;
  • [m.n]Paracyclophanes;
  • Sulfone pyrolysis;
  • Ring contraction

Abstract

Preparatively satisfactory routes to [3.2]paracyclophane (10), [4.2]paracyclophane (14), [4.3]paracyclophane (19) as well as several derivatives of these compounds – among others the bromides 25, the ester 31, the diesters 40–43 – are described using well-established methods of cyclophane chemistry (ring-closure reactions leading to thiacyclophanes, ring contraction by sulfone pyrolysis). The parent systems and their derivatives are now available in gram quantities allowing a study of their chemical properties.(© Wiley-VCH Verlag GmbH & Co. KGaA, 69451 Weinheim, Germany, 2009)

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