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Thiomethylation of amino alcohols using formaldehyde and hydrogen sulfide

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Abstract

Three-component condensations of formaldehyde with hydrogen sulfide and hydroxylamine or amino alcohols at a ratio of 3:2:1 give 47–73% of N-hydroxy(or hydroxyalkyl)-1,3,5-dithiazinanes. The reactions of CH2O with H2S and hydroxylamine or α-amino alcohols at a ratio of 4:3:1 involve both amino and hydroxy groups, leading to the corresponding dithiazinanes. 4-Aminobutan-1-ol reacts with CH2O and H2S under analogous conditions only at the amino group to form 4-(1,3,5-dithiazinan-5-yl)butan-1-ol.

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Authors and Affiliations

  1. Institute of Petroleum Chemistry and Catalysis, Russian Academy of Sciences, pr. Oktyabrya 141, Ufa, 450075, Bashkortostan, Russia

    V. R. Akhmetova, G. R. Nadyrgulova, T. V. Tyumkina, R. V. Kunakova & U. M. Dzhemilev

  2. Nesmeyanov Institute of Organometallic Compounds, Russian Academy of Sciences, Moscow, Russia

    Z. A. Starikova & M. Yu. Antipin

Authors
  1. V. R. Akhmetova
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  2. G. R. Nadyrgulova
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  3. T. V. Tyumkina
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  4. Z. A. Starikova
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  5. M. Yu. Antipin
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  6. R. V. Kunakova
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  7. U. M. Dzhemilev
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Additional information

Original Russian Text © V.R. Akhmetova, G.R. Nadyrgulova, T.V. Tyumkina, Z.A. Starikova, M.Yu. Antipin, R.V. Kunakova, U.M. Dzhemilev, 2007, published in Zhurnal Organicheskoi Khimii, 2007, Vol. 43, No. 6, pp. 919–926.

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Akhmetova, V.R., Nadyrgulova, G.R., Tyumkina, T.V. et al. Thiomethylation of amino alcohols using formaldehyde and hydrogen sulfide. Russ J Org Chem 43, 918–925 (2007). https://doi.org/10.1134/S1070428007060218

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  • DOI: https://doi.org/10.1134/S1070428007060218

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