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Substitutions- und Additionsreaktionen an Spiro-oxiranen

Substitution and addition reactions at spiro-oxiranes

  • Organische Chemie Und Biochemie
  • Published:
Monatshefte für Chemie / Chemical Monthly Aims and scope Submit manuscript

Abstract

Nucleophilic substitution at the spiro carbon atom as well as the CH2-group takes place with spiro-oxiranes1,6 and7, whose spiro carbon atom bear electron withdrawing substituents. In some cases by elimination of formaldehyde a transformation to the corresponding reductone systeme (5,11,16) is observed. In other cases, e.g. with tertiary amines, betaines (2,9,12) are formed, which by elimination of the base rearrange to dioxolenes (3,10). Addition of polar reagents like aryl isocyanate or chloral leads to ring expansion of the threemembered ring to form the five ring systems17,18,20,22 or24.

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Authors and Affiliations

  1. Institut für Organische Chemie, Karl-Franzens-Universität Graz, A-8010, Graz, Österreich

    Hannes Siegel & Helga Wittmann

Authors
  1. Hannes Siegel
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  2. Helga Wittmann
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Herrn emer. o. Univ. Prof. Dr.Erich Ziegler, Institut für Organische Chemie, Karl-Franzens-Universität Graz, mit besten Wünschen zur Vollendung des 70. Lebensjahres gewidmet.

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Siegel, H., Wittmann, H. Substitutions- und Additionsreaktionen an Spiro-oxiranen. Monatsh Chem 113, 1005–1017 (1982). https://doi.org/10.1007/BF00799242

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  • DOI: https://doi.org/10.1007/BF00799242

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