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Rearrangements—Synthetic Reactions “Not Liable” to Retrosynthetic Analysis

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Organic Chemistry from Retrosynthesis to Asymmetric Synthesis

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Abstract

Molecular rearrangements are not amenable to retrosynthesis because of their complex mechanisms. Still, in some cases retro-rearrangements are a conceivable and useful approach to selected target molecules. In this chapter, arguments for the retrosynthetic approach to some well-known rearrangements, Beckmann, Hofmann, Arndt-Eistert, Favorskii, pinacol and Bayer-Villiger, are presented. The mechanism of these rearrangements is explained. Retrosynthesis and synthesis, which include a specific rearrangement in the key step, are proposed for selected target molecules, among them paracetamol, dinestrol and spasmolytic biphenyl carboxylic acid.

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Author information

Authors and Affiliations

  1. Croatian Academy of Sciences and Arts, Zagreb, Croatia

    Vitomir Šunjić

  2. Faculty of Science, University of Zagreb, Zagreb, Croatia

    Vesna Petrović Peroković

Authors
  1. Vitomir Šunjić
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  2. Vesna Petrović Peroković
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Correspondence to Vitomir Šunjić .

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Šunjić, V., Petrović Peroković, V. (2016). Rearrangements—Synthetic Reactions “Not Liable” to Retrosynthetic Analysis. In: Organic Chemistry from Retrosynthesis to Asymmetric Synthesis. Springer, Cham. https://doi.org/10.1007/978-3-319-29926-6_8

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