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Kolbe-Schmitt reaction of sodium 2-naphthoxide

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Abstract

The mechanism of the Kolbe-Schmitt reaction of sodium 2-naphthoxide is examined by means of the B3LYP/LANL2DZ method. After the initial formation of sodium 2-naphthoxide-CO2 complex, the carbon of the CO2 moiety performs an electrophilic attack on the naphthalene ring. Further transformations lead to the formation of sodium 2-hydroxy-1-naphthoate. Sodium 3-hydroxy-2-naphthoate is formed by a 1,3-rearrangement of the CO2Na group. Our findings are in good agreement with the experimental results on the carboxylation reaction of sodium 2-naphthoxide.

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Authors and Affiliations

  1. Faculty of Agronomy, University of Kragujevac, Čačak, Serbia

    Zoran Marković

  2. Faculty of Science, University of Kragujevac, Kragujevac, Serbia

    Svetlana Marković & Igor Đurović

Authors
  1. Zoran Marković
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  2. Svetlana Marković
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  3. Igor Đurović
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Correspondence to Svetlana Marković.

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Correspondence: Svetlana Marković, Faculty of Science, University of Kragujevac, 34000 Kragujevac, Serbia

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Marković, Z., Marković, S. & Đurović, I. Kolbe-Schmitt reaction of sodium 2-naphthoxide. Monatsh Chem 139, 329–335 (2008). https://doi.org/10.1007/s00706-007-0771-6

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