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New method for the synthesis of 1-aminoalkylphosphonic acids Communication 1

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

Summary

  1. 1.

    The reaction of aldehydes with dialkyl hydrogen phosphites and ammonia has been investigated and it has been established that when heat is applieda-aminoalkylphosphonic esters are formed; on hydrolysis these yield the free acids.

  2. 2.

    By this methoda-amino phosphonic acids have been synthesized from benzaldehyde, p-tolualdehyde, p-isopropylbenzaldehyde, p-anisaldehyde, piperonal, and vanillin.

  3. 3.

    It has been shown that benzaldehyde reacts with dialkyl hydrogen phosphites and ammonia in the cold with formation ofa-hydroxybenzylphosphonic esters, which, on being heated with ammonia, are converted intoa-aminobenzylphosphonic esters.

  4. 4.

    A mechanism has been proposed for the reaction, in whicha-hydroxyalkylphosphonic esters play the part of intermediate products. A parallel has been drawn between the reaction observed and other reactions: Zelinsky's reaction, Rodionov's reaction, and the formation ofa-amino sulfonic acids from aldehydes and ammonium bisulfate.

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Literature cited

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Authors and Affiliations

  1. Institute of Organic Chemistry of the USSR Academy of Sciences, Russia

    M. I. Kabachnik & T. Ya. Medved

Authors
  1. M. I. Kabachnik
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  2. T. Ya. Medved
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Kabachnik, M.I., Medved, T.Y. New method for the synthesis of 1-aminoalkylphosphonic acids Communication 1. Russ Chem Bull 2, 769–777 (1953). https://doi.org/10.1007/BF01178856

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  • DOI: https://doi.org/10.1007/BF01178856

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