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On the Route to the N-Phosphoryl Sulfamic Acid

Identyfikatory
Warianty tytułu
Języki publikacji
EN
Abstrakty
EN
Synthesis of the previously unknown N-diethyl phosphorosulfamate 15 was accomplished by direct sulfamation of diethyl phosphoroamidate 4 with sulfur trioxide-DMF coplex 14. The acid 15 was isolated in form of benzyl-16 and cyclohexylamonium 17 salts, which were found to be unstable in water solution. The other possible routes to sulfamate 15 were briefly tested.
Rocznik
Strony
785--791
Opis fizyczny
Bibliogr. 17 poz., rys.
Twórcy
  • Centre of Molecular and Macromolecular Studies, Polish Academy of Sciences, 90-363 Łódź, Sienkiewicza 112, Poland
  • Centre of Molecular and Macromolecular Studies, Polish Academy of Sciences, 90-363 Łódź, Sienkiewicza 112, Poland
Bibliografia
  • 1. Benson G.A. and Spillane W.J., Chem.Rev., 80, 151 (1980).
  • 2. Benson G.A. and Spillane W.J., Sulphamic Acid and Derivatives, in S. Patai and Z. Rappoport (eds), The Chemistry of Sulphonic Acids Esters and Their Derivatives, Interscience Publication, Wiley, Chichester, p. 947-1036(1991).
  • 3. Johnson C.R., Sulphinylamines and Sulphonylamines, in Barton D.H.R. and Ollis W.D., (eds), Comprehensive Organic Chemistry, Pergamon Press, Vol. 3, p. 241 (1979); Kloek J.A. and Leschinsky K.L., J. Org. Chem., 45, 721 (1980); Tomus I. and Schaumann E., Tetrahedron, 725 (1996); Tomus I., Schaumann E. and Adiwidjaja G., J. Chem. Soc., Perkin Trans. 1, 1629 (1996).
  • 4. Atkins G.M. Jr. and Burgess E.M., J. Am. Chem. Soc., 89, 2502 (1967); Atkins G.M. Jr. and Burgess E.M., J. Am. Chem. Soc., 90, 4744 (1968); Tsuge O. and Iwanami S., Bull. Chem. Soc. Jpn., 43, 3543 (1970); Atkins G.M. Jr. and Burgess E.M., J. Am. Chem. Soc., 94 6135 (1972); Hiraoka T. and Kobayashi T., J. Am. Chem. Soc., 48, 480 (1975); Tomus I., Schaumann E., Mayer R. and Adiwidjaja G., Liebigs Ann. Chem., 1975 (1995).
  • 5. Mielniczak G. and Lopusinski A., Heteroatom Chem., 10 (1), 61 (1999).
  • 6. Mielniczak G. and Lopusinski A., Polish J. Chem.,73, 1947 (1999).
  • 7. Grignon-Dubois M., Pillot J.P., Dunoges J., Duffant N. and Calas R., J. Organomet. Chem., 59, 145 (1973); Grignon-Dubois M., Dunoges J. and Cals R., Tetrahedron Lett., 1197 (1976); Burgeois P. and Duffant N., Bull. Soc. Chim. Fr., II, 195 (1980).
  • 8. Bieber T., J. Am. Chem. Soc., 75, 1406 (1953); Hamprecht G. and Mangold D., German Pat., 216476 (1971); Koenig K.H. and Hamprecht G., German Pat., 2514937 (1975) Kloek J.A. and Leschinsky K.L., J. Org. Chem., 41, 4028 (1976).
  • 9. Shokol W.A., Mikhailov N.K. and Molavko L.I., Zh. Obshch. Khim., 47, 2202 (1977).
  • 10. Atherton F.R., Openshaw H.T. and Todd A.R., J. Chem. Soc., 660 (1945).
  • 11. Zwierzak A., Synthesis, 920 (1982).
  • 12. Duffant N., Calas R. and Dunoges J., Bull. Soc. Chim. Fr., 512 (1963).
  • 13. Suter C.H., Evans P.B. and Kiefer J.M., J. Am. Chem. Soc., 60, 538 (1937).
  • 14. Hofmann K. and Simchen G., Synthesis, 699 (1979); Wuts P.G.M. and Wilson K.E., Synthesis 1593 (1998).
  • 15. Gabrecht W.L., J. Org. Chem., 24, 268 (1959).
  • 16. Zwierzak A. and Pilichowska S., Synthesis, 10, 922 (1982).
  • 17. Breuer G. and Schnitzer J., Monatsh. Chem., 68, 301 (1936).
Typ dokumentu
Bibliografia
Identyfikator YADDA
bwmeta1.element.baztech-article-BUJ2-0011-0041
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