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A paradoxical case of dieckmann cyclisation

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An Erratum to this article was published on 01 September 1957

Summary

The isomerisation of ethyl 1-ethoxycarbonyl-2-oxocyclopentylacetate to ethyl 3-ethoxycarbonyl-2-oxocyclopentylacetate has been shown to proceedvia diethyl β-ethoxycarbonylpimelate. The mechanism proposed by Chakravarti1 is untenable. A mechanism based on the equilibrium nature of the reaction has been formulated to explain the formation of ethyl 3-oxocyclohexane-1: 2-dicarboxylate or ethyl 3-ethoxycarbonyl-2-oxocyclopentyl-acetate, as the major product, from diethyl β-ethoxycarbonylpimelate under different experimental conditions of Dieckmann cyclisation. Other mechanisms have also been discussed.

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Authors and Affiliations

  1. Departments of Organic Chemistry, Indian Institute of Science, Bangalore

    D. K. Banerjee, J. Dutta & G. Bagavant

  2. Jadavpur University, Calcutta

    D. K. Banerjee, J. Dutta & G. Bagavant

Authors
  1. D. K. Banerjee
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  2. J. Dutta
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  3. G. Bagavant
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Additional information

An erratum to this article is available at http://dx.doi.org/10.1007/BF03045967.

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Banerjee, D.K., Dutta, J. & Bagavant, G. A paradoxical case of dieckmann cyclisation. Proc. Indian Acad. Sci. 46, 80–93 (1957). https://doi.org/10.1007/BF03045948

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  • DOI: https://doi.org/10.1007/BF03045948

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