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Synthetic Communications
An International Journal for Rapid Communication of Synthetic Organic Chemistry
Volume 38, 2008 - Issue 21
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Original Articles

Trichloroisocyanuric Acid–KF as an Efficient Reagent for One-Pot Synthesis of Dialkylfluorophosphates from Dialkylphosphites

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Pages 3760-3765 | Received 18 Mar 2008, Published online: 14 Oct 2008

REFERENCES

  • (a) Gerstenberger , M. R. C. ; Haas , A. Methods of fluorination in organic chemistry . Angew Chem. Int. Ed. 1981 , 20 , 647 ; (b) Farooq, O. Fluorination of organochlorophosphorus compounds with alkali metal salts of perfluorinated complex anions, part 2. New J. Chem. 2000, 24, 81; (c) Farooq, O. Fluorination of organodichlorophosphorus compounds with sodium hexafluorosilicate, Part 1. J. Chem. Soc. Perkin Trans. 1 1998, 1, 839; (d) Wozniak, L. A.; Chworos, A.; Pyzowski, J.; Stec, W. J. Base-dependent regioselective and P-stereocontrolled hydrolysis of nucleoside 3′-O-(O-2,4,6-trimethyl-benzolyl methane-phosphonothioates)s. J. Org. Chem. 1998, 63, 9109; (e) Chworos, A.; Wozniak, L. A. A facile conversion of thio- and selenophosphoric acids and their derivatives into fluoridates by means of reaction with silver fluoride. Tetrahedron Lett. 1999, 40, 9337 .
  • (a) Schmutzler , R. Chemie der Phosphorfluoride, XII: Uber Phenyldifluoropfosphin . Chem. Ber. 1965 , 98 , 552 ; (b) Roesky, H. W. Dialkylaminochlorofluorophosphine und bis-diathylamino-fluorophosphin. Inorg. Nucl. Chem. Lett. 1969, 5, 891; (c) Heuer, L.; Sell, M.; Schmutzler, R.; Schomberg, D. Preparation of ortho-substituted aryldifluoro-phosphines, 2-XC6H4PF2 (X = MeO or Me2N), and some of their derivatives: X-ray crystal structure determination of (2-MeOC6H4P)4 and of the platinum complex, Cl2Pt(2-MeOC6H4PF2)2. Polyhedron 1987, 6, 1295; (d) Heuer, L.; Jones, G.; Schmutzler, R.; Schomburg, D. Tetrakis(organodifluorophosphine)platinum(O) and bis(arylphosphonofluoridite-bis(arylphosphonofluoridous acid)-platinum(II) complexes. New J. Chem. 1990, 14, 891 .
  • Dabkowski , W. ; Cramer , F. ; Michalski , J. A new synthesis of phosphorofluoridates of biological interest: The reaction of phosphoroazolides with benzoyl fluoride . Tetrahedron Lett. 1987 , 28 , 3561 .
  • Sierakowski , T. ; Kiddle , J. J. Rapid and efficient solid-supported reagent synthesis of fluorine derivatives of phosphorus (V) compounds . Tetrahedron Lett. 2005 , 46 , 2215 .
  • (a) Juenge , E. C. ; Spangler , P. L. ; Duncan , W. P. The reaction of 1,3,5-trichloro-2,4,6-trioxo-hexahydro-s-triazine with tetrahydrofuran and related cyclic ethers . J. Org. Chem. 1966 , 31 , 3836 ; (b) Juenge, E. C.; Beal, D. A. Direct conversion of ethers to esters by trichloroisocyanuric acid. Tetrahedron Lett. 1968, 9, 5819; (c) Juenge, E. C.; Beal, D. A.; Duncan, W. P. Chlorination of aromatic systems with trichloroisocyanuric acid under polar and free-radical conditions. J. Org. Chem. 1970, 35, 719 .
  • Shakya , P. D. ; Dubey , D. K. ; Pardasani , D. ; Palit , M. ; Gupta , A. K. N,N′- Dichloro bis-(2,4,6-trichlorophenyl) urea (CC-2): An efficient reagent for synthesis of dialkyl chlorophosphates. J. Chem. Res. 2005, 821; (b) Acharya, J.; Shakya, P. D.; Pardasani, D.; Palit, M.; Dubey, D. K.; Gupta, A. K. Surface-mediated solid phase reactions: A simple, efficient, and base-free synthesis of phosphonates and phosphates on Al2O3. J. Chem. Res. 2005, 3, 194; (c) Shakya, P. D.; Dubey, D. K.; Pardasani, D.; Palit, M.; Gupta, A. K. A solid supported, rapid and mild synthesis of CWC related phosphoramidates. Catal. Commun. 2005, 6, 669; (d) Gupta, A. K.; Palit, M.; Pardasani, D.; Shakya, P. D.; Shrivastava, R. K.; Dubey, D. K. Micro-synthesis and electron ionization mass spectral analysis of O-alkyl N,N-dialkylphosphoramidocyanidates. Eur. J. Mass Spectrom. 2005, 10, 309; (e) Gupta, A. K; Acharya, J.; Dubey, D. K; Kaushik, M. P. Efficient and convenient one-pot synthesis of phosphoramidates and phosphates. Synth. Commun. 2007, 37, 3403.

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