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Interaction of Mannich bases with triethyl phosphite

Communication 5. Mechanism of the reaction of triethyl phosphite with Mannich ketone bases

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

Conclusions

  1. 1.

    The kinetics of the reaction in the system of Mannich ketone base — triethyl phosphite — salt-forming agent was studied as a function of the nature of the latter. The rate constants of reactions of elimination and substitution depend little on the nature of the salt-forming agent.

  2. 2.

    On the basis of the kinetic data obtained in this and our previous Communications, a general scheme of the mechanism of reactions proceeding in the system of Mannich ketone base — triethyl phosphite — salt-forming agent was proposed. The key step in this scheme is the primary nucleophilic addtion of the anion of the acid to the carbonyl carbon atom with the formation of an intermediate compound, which is considered to be responsible for the occurrence of the reaction as a whole.

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Translated from Izvestiya Akademii Nauk SSSR, Seriya Khimicheskaya, No. 5, pp. 1022–1026, May, 1969.

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Ivanov, B.E., Zheltukhin, V.F. Interaction of Mannich bases with triethyl phosphite. Russ Chem Bull 18, 933–936 (1969). https://doi.org/10.1007/BF00922844

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  • DOI: https://doi.org/10.1007/BF00922844

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