Unexpected Non-Stability of Aminophosphonates: Limitation of Their Synthesis Using Diphenylmethylamine Procedure

• Autorzy: Zoń J. , Miziak P. , Rychlewski T. , Gancarz R.
• Języki publikacji: EN

Abstrakty

EN

New diethyl 1-diphenylmethylaminoalkylphosphonates from aldehydes, ketones, diphenyl methylamine and diethyl phosphite were obtained. Their stability in acidic media as determined by 31P NMR spectroscopy strongly depends on the basicity of the nitrogen atom. The bulky N-substituent can drastically decrease the stability of the ester during acidic hydrolysis leading to decomposition products in the retro Kabachnik-Fields like reaction.

Słowa kluczowe

EN

diphenylmethylamine; hydrophosphonylation; diethyl 1-(diphenylmethylamino) alkylphosphonates; 1-aminoindane-1-phosphonic acid; carbon–phosphorous bond cleavage

• Wydawca: Polskie Towarzystwo Chemiczne
• Czasopismo: Polish Journal of Chemistry
• Rocznik: 2007
• Tom: Vol. 81, nr 11
• Strony: 2023--2030
• Opis fizyczny: Bibligr. 11 poz., rys.

Twórcy

autor

Zoń J.

autor

Miziak P.

autor

Rychlewski T.

autor

Gancarz R.

• Wrocław University of Technology, Faculty of Chemistry, Department of Medicinal Chemistry and Microbiology, Wybrzeże Wyspiańskiego 27, 50-370 Wrocław, Poland fax: [phone],

Bibliografia

• 1. Zon J., Szefczyk B., Sawka-Dobrowolska W., Gancarz R., Kucharska-Zon M., Latajka R., Amrhein N., Miziak P. and Szczepanik W., New J. Chem., 28, 1048 (2004).
• 2. Zon J., Miziak P., Amrhein N. and Gancarz R., Chem. Biodiversity, 2, 1187 (2005).
• 3. Kluczyk A., Szefczyk B., Amrhein N. and Zon J., Polish J. Chem., 79, 583 (2005).
• 4. Miziak P., Zon J., Amrhein N. and Gancarz R., Phytochemistry, 68, 407 (2007).
• 5. Zon J. and Amrhein N., Liebigs Ann. Chem., 625 (1992).
• 6. Zon J., Amrhein N. and Gancarz R., Phytochemistry, 59, 9 (2002).
• 7. Kafarski P. and Zon J., mAminophosphonic and Aminophosphinic Acids. Chemistry and Biological Activity, (eds. Kukhar V.R, Hudson H.R.), Synthesis of a-Aminoalkanephosphonic and a-Aminoalkanephosphinic Acids, John Wiley, Chichester, 2000; pp. 33-74.
• 8. Green D., Patel G., Elgendy S., Baban J.A., Claeson G., Kakkar V.V. and Deadman J., Tetrahedron, 50,5099(1994).
• 9. Deron A., Gancarz R., Gancarz L, Halama A., Kuźma Ł., Rychlewski T. and Zen J., Phosphorus, Sulfur and Silicon, 144-146, 437 (1999).
• 10. Rychlewski T. and Zon J., Phosphorus, Sulfur and Silicon, 147, 463 (1999).
• 11. Doskocz M., Miziak P. and Gancarz R., Polish J. Chem., 79, 547 (2005).