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Volumn 47, Issue 20, 2006, Pages 3341-3344

Stereochemistry of 1-hydroxyphosphonate-phosphate rearrangement. Retention of configuration at the phosphorus atom

Author keywords

Nucleophilic substitution; Phosphonate phosphate rearrangement; Reaction mechanism; retro Abramov reaction; Stereochemistry

Indexed keywords

1 HYDROXYPHOSPHONATE PHOSPHATE; ACETONITRILE; PHOSPHONIC ACID DERIVATIVE; PHOSPHORUS; TRIETHYLAMINE; UNCLASSIFIED DRUG;

EID: 33748335560     PISSN: 00404039     EISSN: None     Source Type: Journal    
DOI: 10.1016/j.tetlet.2006.03.103     Document Type: Article
Times cited : (19)

References (38)
  • 20
    • 84941842967 scopus 로고
    • and references cited therein
    • Pudovik A.N., and Zimin M.G. Pure Appl. Chem. 52 (1980) 989-1011 and references cited therein
    • (1980) Pure Appl. Chem. , vol.52 , pp. 989-1011
    • Pudovik, A.N.1    Zimin, M.G.2
  • 30
    • 33748292604 scopus 로고    scopus 로고
    • note
    • 31P NMR. After completion of the reaction (approximately 2 h) the solution was evaporated to dryness. The crude product was subjected to several crystallizations from dichloromethane to give pure 1a and 1b with a yield above 90%. Synthesis of phosphate 2: 1.9 g (5 mmol) of 1-hydroxyphosphonate 1a and 0.5 g (5 mmol) of triethylamine in dry acetonitrile (40 mL) were heated in a sealed glass ampoule for 15 h at 65 °C. The crude product precipitated at room temperature, then was filtered off and crystallized from dichloromethane/toluene or toluene to give 2 in 96% yield.
  • 31
    • 33748334842 scopus 로고    scopus 로고
    • note
    • 6)...
  • 32
    • 33748317605 scopus 로고    scopus 로고
    • note
    • o > 4σ, collected on Smart APEX (Bruker) at 300 K. Crystallographic data have been deposited at the Cambridge Crystallographic Data Centre, Cambridge, UK. Copies of the data can be obtained, free of charge, on application to CCDC, 12 union Road, Cambridge CB2 1EZ, UK [fax: +44 (0) 1223 336033 or e-mail deposit@ccdc.cam.ac.uk].
  • 33
    • 0001720136 scopus 로고
    • [Angew. Chem., Int. Ed. Engl. 1966, 5, 385-415, 511]
    • Cahn R.S., Ingold C.K., and Prelog V. Angew. Chem. 78 (1966) 413-447 [Angew. Chem., Int. Ed. Engl. 1966, 5, 385-415, 511]
    • (1966) Angew. Chem. , vol.78 , pp. 413-447
    • Cahn, R.S.1    Ingold, C.K.2    Prelog, V.3
  • 37
    • 33748303891 scopus 로고    scopus 로고
    • Scheldrick, G. M. shelxs: Program for Crystal Structure Solution; University of Götingen, Germany, 1997.
  • 38
    • 33748324249 scopus 로고    scopus 로고
    • Scheldrick, G. M. shelxs: Program for Refinement of Crystal Structures; University of Götingen, Germany, 1997.


* 이 정보는 Elsevier사의 SCOPUS DB에서 KISTI가 분석하여 추출한 것입니다.