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Geminal systems Communication 20. Structure and properties of aminomethylphosphonium salts

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

Conclusion

  1. 1.

    The arguments for the phosphonium-phosphorane equilibrium involving the formation of a tricyclic phosphorane previously proposed for phosphonium salt cations R3 \(\mathop P\limits^ +\)CH2X (X=R2N, RO, HO, RS), were examined. This proposal was rejected in light of a) the observed nonequivalence of the isopropyl group methyl protons of [i-Pr2(Me)\(\mathop P\limits^ +\)CH2N(CH2CH2)2O] I− in its PMR spectrum in C5D5N solution, b) x-ray structural analysis of this salt (N⋯P distance 2.69(2) Å), and c) the configurational stability of [o-MeOC6H4 \(\mathop P\limits^ \oplus\)(Me)Pr2-i] I⊖ Up to 190°C. 2. Aminomethylphosphonium salts have aminomethylating action relative to MeO⊖, while phosphineomethylammonium salts do not react with Me.

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Authors and Affiliations

  1. Institute of Chemical Physics, Academy of Sciences of the USSR, Moscow

    R. G. Kostyanovskii, Yu. I. Él'natanov, Sh. M. Shikhaliev, S. M. Ignatov, I. I. Chervin, Sh. S. Nasibov, A. B. Zolotoi, O. A. D'yachenko & L. O. Atovmyan

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  1. R. G. Kostyanovskii
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  2. Yu. I. Él'natanov
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  3. Sh. M. Shikhaliev
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  4. S. M. Ignatov
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  5. I. I. Chervin
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  6. Sh. S. Nasibov
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  7. A. B. Zolotoi
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  8. O. A. D'yachenko
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  9. L. O. Atovmyan
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Additional information

Translated from Izvestiya Akademii Nauk SSSR, Seriya Khimicheskaya, No. 10, pp. 2354–2363, October, 1982.

For Communication 19, see our previous work [1].

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Kostyanovskii, R.G., Él'natanov, Y.I., Shikhaliev, S.M. et al. Geminal systems Communication 20. Structure and properties of aminomethylphosphonium salts. Russ Chem Bull 31, 2073–2080 (1982). https://doi.org/10.1007/BF00950658

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  • DOI: https://doi.org/10.1007/BF00950658

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