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A synthesis of N-alkyl and N,N-dialkyl O-ethyl thiocarbamates from diethyl dixanthogenate using different oxidants

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Abstract

A novel synthesis of N-alkyl and N,N-dialkyl O-ethyl thiocarbamates from diethyl dixanthogenate and primary and secondary amines, using three oxidizing systems, has been developed on the laboratory scale, and the method using sodium hypochlorite has been applied on a semi-industrial scale. The effect of the oxidizing agents, sodium hypochlorite, in-situ-generated peracetic acid, and the manganese(II) acetate/oxygen system on product purity and yield was studied. The results obtained by use of these three methods were compared with those obtained by reaction of sodium ethyl xanthogenacetate and amines, and of sodium ethyl xanthate with amines in the presence of sulfated nickel zeolite catalyst. The reaction mechanism of sodium hypochlorite oxidation has been established on the basis of isolation of reaction intermediates and determination of their structure by use of Fourier-transform infrared, 1H and 13C NMR, and mass spectrometric methods. The suggested sodium hypochlorite and manganese(II) acetate/oxygen systems have many advantages in comparison with commercial and catalytically promoted synthetic methods, because they are new ecologically friendly syntheses.

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Acknowledgments

This work was supported by the Ministry of Science and Technological Development of Serbia (Project Number 142063).

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Authors and Affiliations

  1. Economics Institute, Kralja Milana 16, 11000, Belgrade, Serbia

    Milutin M. Milosavljević

  2. Institute Kirilo Savić, Vojvode Stepe 5, 11000, Belgrade, Serbia

    Milica Sovrlić

  3. Faculty of Technology and Metallurgy, University of Belgrade, Karnegijeva 4, P.O. Box 3503, 11120, Belgrade, Serbia

    Aleksandar D. Marinković

  4. High Chemical Technological School, Kosančićeva 36, 37000, Kruševac, Serbia

    Dragan D. Milenković

Authors
  1. Milutin M. Milosavljević
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  2. Milica Sovrlić
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  3. Aleksandar D. Marinković
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  4. Dragan D. Milenković
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Correspondence to Dragan D. Milenković.

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Milosavljević, M.M., Sovrlić, M., Marinković, A.D. et al. A synthesis of N-alkyl and N,N-dialkyl O-ethyl thiocarbamates from diethyl dixanthogenate using different oxidants. Monatsh Chem 141, 749–755 (2010). https://doi.org/10.1007/s00706-010-0328-y

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  • DOI: https://doi.org/10.1007/s00706-010-0328-y

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