Aryl H-phosphonates. 7. Studies on the formation of phosphorus-carbon bond in the reaction of trityl and benzyl halides with dialkyl and diphenyl H-phosphonates

Tetrahedron

Volumn 53, Issue 37, 1997, Pages 12691-12698

  Kers, Annika ^a   Stawiński, Jacek ^a   Dembkowski, Leszek ^b   Kraszewski, Adam ^c  

^a STOCKHOLM UNIVERSITY   (Sweden)

^b GDANSK UNIVERSITY OF TECHNOLOGY   (Poland)

^c INSTITUTE OF BIOORGANIC CHEMISTRY   (Poland)

Author keywords

[No Author keywords available]

Indexed keywords

PHOSPHONIC ACID DERIVATIVE;

ARTICLE; DRUG SYNTHESIS; IN VITRO STUDY; NUCLEAR MAGNETIC RESONANCE SPECTROSCOPY; PRIORITY JOURNAL; REACTION ANALYSIS; STEREOCHEMISTRY;

EID: 0343052544     PISSN: 00404020     EISSN: None     Source Type: Journal    
DOI: 10.1016/S0040-4020(97)00790-4     Document Type: Article

References (32)

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23. Recently, a bromothiophosphate was isolated from the products of a similar type of reaction involving 1-bromo-2,2-diphenylcyclocarboxylate and sodium salt of 2-mercapto-5,5-dimethyl-1,3,2-dioxaphosphinane in THF. See, L. Dembkowski and J. Rachon, Phosphor. Sulfur Silicon., 111, 1996, 826.
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27. In acetonitrile in the presence of TEA (15 equiv.) the disproportionation of 1b goes to completion within few minutes.
28. To the present time, only formation of alkali metal salts of H-phosphonate diesters have been reported. The absence of detectable P-H couplings prevents more detail NMR analysis of the signal at ∼139 ppm. However, the value of its chemical shift and the observed reactivity of a species that gave rise to it, are in agreement with the postulated structure 2b.
29. The bromophosphate 4b is not stable under the reaction conditions and undergoes some further transformations. However, the pattern of resonances in the reaction mixture paralleled those produced upon treatment of an authentic sample of 4b with DBU. In the initial stages of the latter reaction, the formation of a singlet at ∼-4.8 ppm, assigned to 5b, was observed. As expected, an analogous signal was also detected upon treatment of diphenyl phosphorochloridate with DBU in THF.
30. Studies are in progress to elucidate this phenomenon.
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