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Volumn 119, Issue 35, 1997, Pages 8177-8190

Phosphonate diester and phosphonamide synthesis. Reaction coordinate analysis by 31P NMR spectroscopy: Identification of pyrophosphonate anhydrides and highly reactive phosphonylammonium salts

Author keywords

[No Author keywords available]

Indexed keywords

ORGANOPHOSPHORUS COMPOUND; PHOSPHONAMIDE DERIVATIVE; PHOSPHONIC ACID ESTER; UNCLASSIFIED DRUG;

EID: 0030818538     PISSN: 00027863     EISSN: None     Source Type: Journal    
DOI: 10.1021/ja962465o     Document Type: Article
Times cited : (83)

References (103)
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    • (c) For aromatic amine-catalyzed couplings of phosphonodichloridates, see: Doak, G. O.; Freedman, L. D. J. Am. Chem. Soc. 1954, 76, 1621.
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    • While the stability of phosphonamides is thus not a major concern, the lack of (or minimal) double-bond character of the P-N bond of phosphonamides negates a potential plus of phosphonamide haptens over their diester counterparts
    • While the stability of phosphonamides is thus not a major concern, the lack of (or minimal) double-bond character of the P-N bond of phosphonamides negates a potential plus of phosphonamide haptens over their diester counterparts.
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    • 24
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    • (b) For the synthesis of pyrophosphate anhydrides with thionyl chloride and other acyl halides, see: Mason, H. S.; Todd, A. R. J. Chem. Soc. 1951, 2267. Corby, N. S.; Kenner, G. W.; Todd, A. R. J. Chem. Soc. 1952, 1234.
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    • (b) For the synthesis of pyrophosphate anhydrides with thionyl chloride and other acyl halides, see: Mason, H. S.; Todd, A. R. J. Chem. Soc. 1951, 2267. Corby, N. S.; Kenner, G. W.; Todd, A. R. J. Chem. Soc. 1952, 1234.
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    • note
    • 2, 25 °C, 3 h). This difference may in part reflect reduced nucleophilicity as a result of hydrogen bonding between the hydroxyl and the C-terminal carboxyl moiety.
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    • note
    • N2 process in which the rate-determining step involves approach of the nucleophile to the electrophilic phosphorus center. These workers had also shown that basicity of the nucleophile, steric hindrance, and the relative energies of the bonds formed and broken influence the rate-determining step.
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    • 31P shift at 15.3 ppm; however, our earlier results suggest that this species is actually the anhydride: Mucha, A.; Kafarski, P.; Plenat, F.; Cristau, H.-J. Tetrahedron 1994, 50, 12743.
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    • Yamazaki and co-workers have proposed that an acyloxy N-phosphonium salt with pyridine was formed an intermediate in an Arbuzov reaction but the species was uncharacterized: Yamazaki, N.; Niwano, M.; Kawabata, J.; Higashi, F. Tetrahedron 1975, 31, 665.
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    • note
    • 31P NMR spectrum.
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    • note
    • 62
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    • Studies are underway in our laboratory which will explore the synthetic potential and mechanistic aspects of the phosphonylammonium salts more fully
    • Studies are underway in our laboratory which will explore the synthetic potential and mechanistic aspects of the phosphonylammonium salts more fully.
  • 101
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    • 31P NMR could not be carried out because the triethylammonium salts are converted instananeously to product on addition of the nucleophile
    • 31P NMR could not be carried out because the triethylammonium salts are converted instananeously to product on addition of the nucleophile.


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