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Cycloadditions to Alkenyl[2.2]paracyclophanes†

  1. Ashraf A. Aly1,
  2. Sonja Ehrhardt1,
  3. Henning Hopf1,
  4. Ina Dix1,
  5. Peter G. Jones2

Article first published online: 10 NOV 2005

DOI: 10.1002/ejoc.200500396

Issue

European Journal of Organic Chemistry

European Journal of Organic Chemistry

Volume 2006, Issue 2, pages 335–350, January 2006

Additional Information

How to Cite

Aly, A. A., Ehrhardt, S., Hopf, H., Dix, I. and Jones, P. G. (2006), Cycloadditions to Alkenyl[2.2]paracyclophanes. Eur. J. Org. Chem., 2006: 335–350. doi: 10.1002/ejoc.200500396

Author Information

  1. 1

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

  2. 2

    Institut für Anorganische und Analytische Chemie, Technische Universität Braunschweig, Postfach 3329, 38023 Braunschweig, Germany, Fax: +49-531-391-5387

  1. †

    Cyclophanes, LIV. Part LIII: Ref.‡

Publication History

  1. Issue published online: 2 JAN 2006
  2. Article first published online: 10 NOV 2005
  3. Manuscript Received: 3 JUN 2005

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Keywords:

  • Cyclophanes;
  • Cycloadditions;
  • Annelation;
  • Ene reaction

Abstract

Cycloadditions between the 4-alkenyl[2.2]paracyclophanes 7, 16–21 and the dienophiles 10a–h have been studied. Whereas 10a, b, d, and g prefer Diels–Alder addition involving the olefinic double bond and one double bond of a cyclophane benzene ring, 10c, e, f, and h undergo other cycloadditions such as ene reaction (10c), [2+2] cycloaddition to the olefinic double bond (10e) and heterodiene addition to the vinyl substituent (10f, h). Several of the isolated cycloadducts (e.g. 24–26, 52) are valuable substrates for the preparation of annelated cyclophanes. The mechanisms of several of these cycloadditions are discussed. (© Wiley-VCH Verlag GmbH & Co. KGaA, 69451 Weinheim, Germany, 2006)

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