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Reaction between piperidine-4-spiro-2′-oxiranes and nucleophilic reagents

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Chemistry of Heterocyclic Compounds Aims and scope

Abstract

An investigation was made into the opening of the epoxide ring of piperidine-4-spiro-2′-oxiranes by N-, H-, C-, and P-nucleophiles, which yielded the corresponding 3,4-dihydroxy- and 3-hydroxypiperidine derivatives. When these epoxides were reacted with organomagnesium compounds, regrouping occurred, the piperidine ring reducing in size to a pyrrolidine ring and the latter being functionalized by a hydroxymethyl group.

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Authors and Affiliations

  1. Belorussian Technological Institute, Minsk

    A. M. Zvonok & E. B. Okaev

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  1. A. M. Zvonok
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  2. E. B. Okaev
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Translated from Khimiya Geterotsiklicheskikh Soedinenii, No. 11, pp. 1499–1503, November, 1993.

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Zvonok, A.M., Okaev, E.B. Reaction between piperidine-4-spiro-2′-oxiranes and nucleophilic reagents. Chem Heterocycl Compd 29, 1291–1295 (1993). https://doi.org/10.1007/BF00532027

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  • DOI: https://doi.org/10.1007/BF00532027

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