Nucleophilic Displacements in Alkylphosphonates: P–O Versus P–C Bond Cleavage. A Combined DFT and Experimental Study

REFERENCES

• Ando , K. 1999 . J. Org. Chem. , 64 : 6815 – 6821 . and ref. 8 therein
   PubMed Web of Science ®Google Scholar
• 1989 . This reaction is normally feasible only for activated alkylphosphonates. See: Maryanoff, B. E.; Raitz, A. B. . Chem. Rev. , 89 : 863 – 927 .
   Web of Science ®Google Scholar
• Paul , R. M. 1955 . J. Chem. Soc. , : 574 – 584 .
   Web of Science ®Google Scholar
• Burg , A. B. and Sarkis , A. J. 1965 . J. Am. Chem. Soc. , 87 : 238 – 242 .
   Web of Science ®Google Scholar
• Hall , C. R. , Inch , T. D. , Peacock , G. , Pottage , C. and Williams , N. E. 1984 . J. Chem. Soc. Perkin Trans. 1 , : 669 – 674 .
   Google Scholar
• Hammond , P. S. , Kirchner , M. B. and Lieske , C. N. 1990 . J. Org. Chem. , 55 : 6049 – 6051 .
   Web of Science ®Google Scholar
• Hammerschmidt , F. 1993 . Monatsh. Chem. , 124 : 1063 – 1069 .
   Web of Science ®Google Scholar
• Hammerschmidt , F. and Schmidt , S. 2000 . Eur. J. Org. Chem. , : 2239 – 2245 .
   Web of Science ®Google Scholar
• Hawkins , M. J. , Powell , E. T. , Leo , G. C. , Gauthier , D. A. , Greco , M. N. and Marynoff , B. 2006 . Org. Lett. , 8 : 3429 – 3431 .
   PubMed Web of Science ®Google Scholar
• Berry , J. P. , Arnold , J. R. and Isbell , A. F. 1968 . J. Org. Chem. , 33 : 1664 – 1665 .
   Web of Science ®Google Scholar
• Perlikowska , W. , Modro , A. M. , Modro , T. A. and Mphahlele , M. J. 1996 . J. Chem. Soc. Perkin Trans. 2 , : 2611 – 2613 .
   Google Scholar
• Zafrani , Y. , Sod-Moriah , G. and Segall , Y. 2009 . Tetrahedron , 65 : 5278 – 5283 .
   Web of Science ®Google Scholar
• Dejaegere , A. and Karplus , M. 1993 . J. Am. Chem. Soc. , 115 : 5316 – 5317 .
   Web of Science ®Google Scholar
• Dejaegere , A. , Liang , X. and Karplus , M. 1994 . J. Chem. Soc. Faraday Trans. , 90 : 1763 – 1770 .
   Google Scholar
• Chang , N.-Y. and Lim , C. 1997 . J. Phys. Chem. A , 101 : 8706 – 8713 .
   Web of Science ®Google Scholar
• Chang , N.-Y. and Lim , C. 1998 . J. Am. Chem. Soc. , 120 : 2156 – 2167 .
   Web of Science ®Google Scholar
• Florian , J. and Warshel , A. 1998 . J. Phys. Chem. B. , 102 : 719 – 734 .
   Web of Science ®Google Scholar
• Hu , C.-H. and Brinck , T. 1999 . J. Phys. Chem. A , 103 : 5379 – 5386 .
   Web of Science ®Google Scholar
• Lopez , X. , Dejaegere , A. and Karplus , M. 2001 . J. Am. Chem. Soc. , 123 : 11755 – 11763 .
   PubMed Web of Science ®Google Scholar
• Menegon , G. , Loos , M. and Chaimovich , H. 2002 . J. Phys. Chem. A , 106 : 9078 – 9084 .
   Web of Science ®Google Scholar
• Arantes , G. M. and Chaimovich , H. 2005 . J. Phys. Chem. A , 109 : 5625 – 5635 .
   PubMed Web of Science ®Google Scholar
• López , C. S. , Faza , O. N. , de Lera , A. R. and York , D. M. 2005 . Chem. Eur. J. , 11 : 2081 – 2093 .
   PubMed Web of Science ®Google Scholar
• Iché-Tarrat , N. , Barthelat , J.-C. , Rinaldi , D. and Vigroux , A. 2005 . J. Phys. Chem. B. , 109 : 22570 – 22580 .
   PubMed Web of Science ®Google Scholar
• Lopez , X. , Dejaegere , A. , Leclerc , F. , York , D. M. and Karplus , M. 2006 . J. Phys. Chem. B. , 110 : 11525 – 11539 .
   PubMed Web of Science ®Google Scholar
• Thatcher , G. R. J. and Campbell , A. S. 1993 . J. Org. Chem. , 58 : 2272 – 2281 .
   Web of Science ®Google Scholar
• Zheng , F. , Zhan , C.-G. and Ornstein , R. L. 2001 . J. Chem. Soc. Perkin Trans. 2 , : 2355 – 2363 .
   Google Scholar
• Bell , A. J. , Citra , A. , Dyke , J. M. , Ferrante , F. , Gagliardi , L. and Watts , P. 2004 . Phys. Chem. Chem. Phys. , 6 : 1213 – 1218 .
   Web of Science ®Google Scholar
• Barbosa , A. C. P. , Borges , I. Jr and Lin , W. O. 2004 . J. Mol. Struct. (THEOCHEM) , 712 : 187 – 195 .
   Web of Science ®Google Scholar
• Doskocz , M. , Roszak , S. , Majumbar , D. , Doskocz , J. , Gancarz , R. and Leszczynski , J. 2008 . J. Phys. Chem. A , 112 : 2077 – 2081 .
   PubMed Web of Science ®Google Scholar
• McAnoy , A. M. , Paine , M. R. L. and Blanksby , S. J. 2008 . Org. Biomol. Chem. , 6 : 2316 – 2326 .
   PubMed Web of Science ®Google Scholar
• McAnoy , A. M. , Williams , J. , Paine , M. R. L. , Rogers , M. L. and Blanksby , S. J. 2009 . J. Org. Chem. , 74 : 9319 – 9327 .
   PubMed Web of Science ®Google Scholar
• Ashkenazi , N. , Segall , Y. , Chen , R. , Sod-Moriah , G. and Fattal , E. 2010 . J. Org. Chem. , 75 : 1917 – 1926 .
   PubMed Web of Science ®Google Scholar
• Kluger , R. and Taylor , S. D. 1990 . J. Am. Chem. Soc. , 112 : 6669 – 6671 .
   Web of Science ®Google Scholar
• Eymery , F. , Iorga , B. and Savignac , P. 1999 . Tetrahedron , 55 : 13109 – 13320 .
   Web of Science ®Google Scholar
• Ashkenazi , N. , Karton , Y. and Segall , Y. 2004 . Tetrahedron Lett. , 45 : 8003 – 8006 .
   Web of Science ®Google Scholar
• Ashkenazi , N. , Zade , S. S. , Segall , Y. , Karton , Y. and Bendikov , M. 2005 . Chem. Commun. , : 5879 – 5881 .
   PubMed Web of Science ®Google Scholar
• Aksnes , G. and Songstad , J. 1965 . Acta Chem. Scand. , 19 : 893 – 897 .
   Google Scholar
• Aksnes , G. , Gierstae , R. and Wulvik , E. A. 1988 . Phosphorus and Sulfur and the Relat. Elem. , 39 : 141 – 152 .
   Web of Science ®Google Scholar
• van Bochove , M. A. , Swart , M. and Bickelhaupt , F. M. 2006 . J. Am. Chem. Soc. , 128 : 10738 – 10744 .
   PubMed Web of Science ®Google Scholar
• van Bochove , M. A. , Swart , M. and Bickelhaupt , F. M. 2007 . Chem. Phys. Chem. , 8 : 2452 – 2463 .
   Google Scholar
• van Bochove , M. A. and Bickelhaupt , F. M. 2008 . Eur. J. Org. Chem. , : 649 – 654 .
   Google Scholar
• Fedoryński , M. 2003 . Chem. Rev. , 103 : 1099 – 1132 .
   PubMed Web of Science ®Google Scholar
• Parham , W. E. and Schweizer , E. E. 1959 . J. Org. Chem. , 24 : 1733 – 1735 .
   Web of Science ®Google Scholar
• Regen , S. L. and Singh , A. 1982 . J. Org. Chem. , 47 : 1587 – 1588 .
   Web of Science ®Google Scholar
• Basil , S. F. and Gilbert , E. E. 1962 . J. Chem. Eng. Data , 7 : 568 – 569 .
   Google Scholar
• Chien , C.-T. , Tasi , C.-H. , Chang , T.-Y. , Tsai , P.-K. , Wang , Y.-C. and Yan , T.-H. 2006 . J. Org. Chem. , 71 : 4324 – 4327 .
   PubMed Web of Science ®Google Scholar
• DeWeese , F. T. , Minter , D. E. , Nosovitch , J. T. and Michael , G. R. 1986 . Tetrahedron , 42 : 239 – 244 .
   Web of Science ®Google Scholar
• Ledwith , A. and Woods , H. J. 1967 . J. Chem. Soc. B , 10 : 973 – 976 .
   Google Scholar