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Synthesis of (strained) macrocycles by sulfone pyrolysis

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Macrocycles

Part of the book series: Topics in Current Chemistry ((TOPCURRCHEM,volume 161))

Abstract

Among the methods for the synthesis of strained macrocycles, the ring contraction of unstrained cyclic precursors by thermal elimination of sulfur dioxide (“sulfone pyrolysis”) is of general importance because it offers access to a large diversity of macrocycles not equalled by other methods. Highly strained macrocycles as well as macrocycles containing labile moieties or functional groups can be synthesized. Several bonds can be created simultaneously and yields are comparably high.

In order to fully acknowledge the scope of this method, recent pyrolyses are listed and arranged according to structural features. Experimental parameters can be adapted to reactivity and stability of the compounds and are listed for purpose of easy comparison.

By reviewing the reactions listed, it becomes obvious that the potential of this synthetic method is not yet fully explored.

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Authors and Affiliations

  1. Institut für Organische Chemie und Biochemie der Universität Bonn, Gerhard-Domagk-Str. 1, W-5300, Bonn 1, FRG

    Joachim Dohm & Fritz Vögtle

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  1. Joachim Dohm
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  2. Fritz Vögtle
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© 1992 Springer-Verlag

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Dohm, J., Vögtle, F. (1992). Synthesis of (strained) macrocycles by sulfone pyrolysis. In: Macrocycles. Topics in Current Chemistry, vol 161. Springer, Berlin, Heidelberg. https://doi.org/10.1007/3-540-54348-1_8

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  • DOI: https://doi.org/10.1007/3-540-54348-1_8

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  • Publisher Name: Springer, Berlin, Heidelberg

  • Print ISBN: 978-3-540-54348-0

  • Online ISBN: 978-3-540-47581-1

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