Comments on the Synthesis of Aminomethylphosphonic Acid

Synthesis (Germany)

Volumn 1989, Issue 7, 1989, Pages 547-548

  Soroka, Mirosław ^a  

^a WROCLAW UNIVERSITY OF TECHNOLOGY   (Poland)

Author keywords

[No Author keywords available]

Indexed keywords

EID: 0000176550     PISSN: 00397881     EISSN: 1437210X     Source Type: Journal    
DOI: 10.1055/s-1989-27313     Document Type: Article

References (30)

1. Franz, J. E. US Patent 3977860 (1976), Monsanto Co.; C. A. 1977. 86, 43812.
2. Franz, J.E., in: Advances in Pesticide Science, Geissbuehler, H. (ed.), Vol.2, Pergamon Press, Oxford, 1979, p. 139.
3. Roundup Herbicide by Monsanto, Monsanto Co., St. Louis, Mo., U.S.A., 1985, p. 9.
4. Van Gaertner, R., Phillips, W.G. US Patent 4221 583 (1980), Monsanto Co.; C. A. 1981, 94, 4122.
5. Moser, H. US Patent 4369142 (1983), Ciba-Geigy Corp.; C.A. 1983, 98. 179638.
6. Oleksyszyn, J. Polish Patent 120759 (1983); C.A. 1983, 99, 158862.
7. Sales Barquets, R. Spanish Patent 504479 (1982), Industria Espa-nola de Productor Organicos (Orgasa); C.A. 1983, 98, 126382.
8. Pulwer, M.J., Balthazor, T.M. Synth. Commun. 1986, 16, 733.
9. This reaction is another example of the well known amidoalkylation (amidomethvlation) reaction. For examples, see: Ref. 9 11.
10. Zaugg, H.R, Martin, W.B. Org. React. 1965, 14, 52.
11. Zaugg, H.E. Synthesis 1984, 85.
12. Zaugg, H.E. Synthesis 1984, 181.
13. Engelmann, M, Pikl, J. US Patent 2304156 (1942), DuPont; C.A. 1943, 37, 3261.
14. Pikl, J. US Patent 2328358 (1943), DuPont; C.A. 1944. 38, ISA. In both patents (Ref, 12 and 13), a two-step mechanism was proposed: RCONHCH2OH→RCONHCH2OPCl2→RCONHCH2-P(O)CI2→3.
15. We assume that the reaction is a P-amidomethylation reaction with generation of N-acyliminium ion as the crucial step: RCONHCH2OH-RCONHCH2->RCONH =CH2.
16. Chavane, V. Bull. Soc. Chim. Fr. 1948, 774.
17. Brit. Patent 678489 (1952), Cilag Ltd.; C.A. 1954, 48, 741.
18. Hotten, B.W., Johnson, F.O. US Patent 2862882 (1958), California Research Co.; C.A. 1959, 53, 6602.
19. Okamoto, Y., Katakama, T., Sakurai, H. Kogyo Kagaku Zasshi 1967, 70. 604; C.A. 1967, 67, 82242.
20. Oleksyszyn, J., Tyka, R.. Mastalerz, P. Polish Patent 117780 (1982); C.A. 1983, 99. 70992.
21. Soroka, M. Polish Patent 133387 (1983).
22. Tyka, R., Haegele, G. Synthesis 1984. 218. In this paper, the same procedure is applied for the synthesis of iV-alkylaminomethylphos-phonic acid.
23. Silhanek, J, Jezek, F., Zbirovsky, M. Sb. Vys. Sk. Chem. Technol. Praze, Org. Chcm. Technol. 1983, C28, 115; C.A. 1985, 103, 142077.
24. Emmons, W., Rolewicz, H., Cannon, W., Ross, R. J. Am. Own. Soc. 1952, 74, 5524.
25. Ladhar, R, Gharbi, R. El., Delmas, M., Gaset, A. Synthesis 1986. 643.
26. Wegler, R., Ballauf, A. Chem. Ber. 1948, 81. 527.
27. Gradstein, M.A., Pollock, M.W. J. Am. Chem. Soc. 1948. 70. 3079.
28. The reaction of "triacctyl-triazan" with phosphorus acid in tetra-hydrothiophene S.S-dioxidc was mentioned (as example 5) in: Sommer, K., Raab, G. German Patent (DOS) 2829046 (19801, Benckiser-Knapsack AG; C.A. 1980, 92, 215542. The abstract is not indexed in Chemical Substance Index (under phosphonic acid, aminomethyl) nor in Formula Index (under CH6N03P). The author thanks a referee who evaluated the present communication for providing the C.A. reference.
29. Soroka, M., Zygmunt, J. Synthesis 1988, 370.
30. Hellmann, H. Angew. Chem. 1957, 69, 463.