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Reaction of tribenzyl- and triacetyl-levoglucosans with a solution of sodium in liquid ammonia

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Bulletin of the Academy of Sciences of the USSR, Division of chemical science Aims and scope

Summary

  1. 1.

    2,3,4-Tri-O-benzyl-1,6-anhydroglucose reacts with sodium in liquid ammonia with formation of levoglucosan and bibenzyl. No phenolic substances were detected in the reaction products.

  2. 2.

    2,3,4-Tri-O-acetyl-1,6-anhydroglucose reacts with a solution of sodium in liquid ammonia with formation of levoglucosan and acetamide. It was shown that phenol was absent in the reaction products.

  3. 3.

    1,6-Anhydroglucose reacts with sodium in liquid ammonia with formation of an alcoholate, from which 1,6-anhydroglucose is recovered quantitatively when the product is treated with water. On treatment with a large excess of sodium, 1,6-anhydroglucose is partially changed with formation of a resin that does not contain phenols.

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Authors and Affiliations

  1. N. D. Zelinskii Institute of Organic Chemistry, Academy of Sciences, USSR

    G. V. Davydova, M. S. Dobrzhinskaya & N. N. Shorygina

Authors
  1. G. V. Davydova
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  2. M. S. Dobrzhinskaya
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  3. N. N. Shorygina
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Davydova, G.V., Dobrzhinskaya, M.S. & Shorygina, N.N. Reaction of tribenzyl- and triacetyl-levoglucosans with a solution of sodium in liquid ammonia. Russ Chem Bull 12, 796–798 (1963). https://doi.org/10.1007/BF01134727

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  • DOI: https://doi.org/10.1007/BF01134727

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