Studies on the reaction of trityl derivatives with H-phosphonate diesters: Their relevance to the synthesis of 4-pyridylphosphonates

Heteroatom Chemistry

Volumn 10, Issue 6, 1999, Pages 492-499

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

^a STOCKHOLM UNIVERSITY   (Sweden)

^b GDANSK UNIVERSITY OF TECHNOLOGY   (Poland)

^c INSTITUTE OF BIOORGANIC CHEMISTRY   (Poland)

Author keywords

[No Author keywords available]

Indexed keywords

EID: 0003647795     PISSN: 10427163     EISSN: None     Source Type: Journal    
DOI: 10.1002/(SICI)1098-1071(1999)10:6<492::AID-HC10>3.0.CO;2-D     Document Type: Article

References (29)

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21. The reported yields were rather low (30-39%) and the harsh reaction conditions make this method inapplicable to the synthesis of natural product derivatives.
22. 31P NMR).
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25. Diphenyl phosphite anion is apparently a hard nucleophile and thus preferably attacks a hard carbinol center. Soft phosphorus nucleophiles, e.g., phosphines, react with trityl cations at soft, aromatic carbons. See, Bidan et al., Ref. [18].
26. 31P NMR spectrum.
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28. When trityl chloride was used instead of trityl bromide, the reaction went to completion within 15 minutes.
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