Acylphosphonate hemiketals - Formation rate and equilibrium. The electron-withdrawing effect of dimethoxyphosphinyl group

Journal of the Chemical Society. Perkin Transactions 2

Volumn , Issue 2, 1997, Pages 341-349

  Katzhendler, Jehoshua ^a   Ringel, Israel ^a   Karaman, Rafik ^a   Zaher, Hisham ^a   Breuer, Eli ^a  

^a HEBREW UNIVERSITY OF JERUSALEM   (Israel)

Author keywords

[No Author keywords available]

Indexed keywords

EID: 0000734283     PISSN: 03009580     EISSN: None     Source Type: Journal    
DOI: 10.1039/a604196e     Document Type: Article

References (84)

1. Acylphosphonate reviews: Yu. A. Zhdanov, L. A. Uzlova and Z. I. Glebova, Russ. Chem. Rev. (Engl. Transl.), 1980, 94, 843; E. Breuer, in The chemistry of organophosphorus compounds, ed. F. Hartley, Wiley, Chichester, 1996, vol. 4, pp. 653-729.
2. Acylphosphonate reviews: Yu. A. Zhdanov, L. A. Uzlova and Z. I. Glebova, Russ. Chem. Rev. (Engl. Transl.), 1980, 94, 843; E. Breuer, in The chemistry of organophosphorus compounds, ed. F. Hartley, Wiley, Chichester, 1996, vol. 4, pp. 653-729.
3. (a) E. Breuer, R. Karaman, H. Leader, A. Goldblum and R. Moshe, Phosphorus and Sulfur, 1987, 30, 113;
4. (b) E. Breuer, R. Karaman, H. Leader and A. Goldblum, Phosphorus and Sulfur, 1987, 33, 61;
5. (c) E. Breuer, R. Karaman, A. Goldblum and H. Leader, J. Chem. Soc., Perkin Trans. 2, 1988, 2029;
6. (d) R. Karaman, A. Goldblum, E. Breuer and H. Leader, J. Chem. Soc., Perkin Trans 1, 1989, 765.
7. (a) E. Breuer, R. Karaman, D. Gibson, H. Leader and A. Goldblum, J. Chem. Soc., Chem. Commun., 1988, 504;
8. (b) E. Breuer, R. Karaman, A. Goldblum, D. Gibson, H. Leader, B. V. L. Potter and J. H. Cummins, J. Chem. Soc., Perkin Trans. 1, 1988, 3047;
9. (c) E. Breuer, R. Karaman, H. Leader and A. Goldblum, J. Chem. Soc., Chem. Commun., 1987, 671;
10. (d) J. Katzhendler, R. Karaman, D. Gibson, H. Leader and E. Breuer, J. Chem. Soc., Perkin Trans. 2, 1989, 2, 589.
11. (a) G. Golomb, A. Schlossman, H. Saadeh, M. Levi, J. M. Van Gelder and E. Breuer, Pharm. Res., 1992, 9, 143;
12. (b) G. Golomb, A. Schlossman, Y. Eitan, H. Saadeh, J. M. Van Gelder and E. Breuer, J. Pharm. Sci., 1992, 81, 1004;
13. (c) E. Breuer, G. Golomb, A. Hoffman, A. Schlossman, J. M. van Gelder, H. Saadeh, M. Levi and Y. Eitan, Phosphorus, Sulfur, and Silicon, 1993, 76, 167;
14. (d) J. M. van Gelder, E. Breuer, A. Ornoy, A. Schlossman, N. Patlas and G. Golomb, Bone, 1995, 16, 511.
15. (a) R. Kluger and J. Chin, J. Am. Chem. Soc., 1978, 100, 7382;
16. (b) R. Kluger, D. Pike and J. Chin, Can. J. Chem., 1978, 56, 1972;
17. (c) A. Narayanan and K. D. Berlin, J. Am. Chem. Soc., 1979, 101, 109;
18. (d) K. D. Berlin and A. Taylor, J. Am. Chem. Soc. 1964, 86, 3862;
19. (e) E. S. Krol, J. M. Davis and G. R. J. Tatcher, J. Chem. Soc. Chem. Commun., 1991, 118.
20. (a) M. Uieara, C. Zucco, D. Zanette, M. C. Rezende and F. Nome, J. Chem. Soc., Perkin Trans. 2, 1987, 175;
21. (b) J. Druzian, C. Zucco, M. C. Rezende and F. Nome, J. Org. Chem., 1989, 59, 4767;
22. (c) C. Gustafson and M. Johanson, Acta Chem. Scand., 1948, 2, 42.
23. J. March, Advanced organic chemistry, McGraw-Hill, New York, 1977, 2nd edn., p. 575.
24. (a) K. D. Berlin, R. T. Claunch and E. T. Gaudy, J. Org. Chem., 1968, 33, 3090;
25. (b) G. Holan, W. M. P. Johnson, K. Rihs and C. T. Virgona, Pestic. Sci., 1984, 15, 361.
26. 15
27. (a) R. P. Bell, Adv. Phys. Chem., 1966, 4, 1;
28. (b) S. Patai, The Chemistry of Carbonyl Group, vol. II, Interscience, London, 1970, p. 1;
29. (c) J. E. Meany and Y. Pocker, J. Am. Chem. Soc., 1991, 113, 6155;
30. (d) P. Greenzaid, J. Org. Chem., 1973, 18, 3164;
31. (e) R. P. Bell and P. E. Sorensen, J. Chem. Soc., Perkin Trans. 2, 1976, 1594.
32. M. M. Davies, Trans. Faraday Soc., 1940, 86, 1114.
33. H. Shechter and F. Courad, J. Am. Chem. Soc., 1950, 72, 3371.
34. A. L. Henne, M. S. Newman, L. L. Quill and R. A. Staniforth, J. Am. Chem. Soc. 1947, 69, 1819.
35. (a) F. Swarts, Bull. Soc. Chim. Belg., 1929, 35, 414;
36. (b) M. L. Bender, J. Am. Chem. Soc. 1953, 75, 5986;
37. (c) A. Moffat and H. Hunt, J. Am. Chem. Soc., 1959, 81, 2082; J. Chem. Soc., Chem. Commun., 1977, 857.
38. (c) A. Moffat and H. Hunt, J. Am. Chem. Soc., 1959, 81, 2082; J. Chem. Soc., Chem. Commun., 1977, 857.
39. (a) G. Fraenkel and D. Watson, J. Am. Chem. Soc., 1976, 97, 231;
40. (b) A. Cipiciani, P. Linda and G. Savelli, J. Chem. Soc., Chem. Commun., 1977, 857.
41. (a) R. Wolfenden, Ann. Rev. Biophys. Bioeng., 1976, 5, 271;
42. (b) R. Wolfenden and L. Frick, in Enzyme Mechanisms, eds. M. I. Page and A. Williams, 1987, RSC, London, p. 97;
43. (c) A. Tramontano, A. A. Amman and R. A. Lerner, J. Am. Chem. Soc., 1988, 110, 2282;
44. (d) J. Jacobs, P. G. Schultz, R. Sugasawara and M. Powell, J. Am. Chem. Soc., 1987, 109, 2174;
45. (e) A. P. Kaplan and P. A. Bartlett, Biochemistry, 1991, 30, 8165.
46. D. H. Aue and M. T. Bowers, Gas phase ion chemistry, ed. M. T. Bowers, Academic Press, New York, 1979, vol. 2, ch. 9.
47. S. Olivella, F. Urpi and J. Vilarrassa, J. Comput. Chem., 1984, 5, 230.
48. M. J. S. Dewar and W. Thiel, J. Am. Chem. Soc., 1977, 99, 4899.
49. (a) A. Goldblum, J. Comput. Chem., 1987, 8, 835;
50. (b) K. Ya. Burstein and A. N. Isaev, Theor. Chim. Acta, 1984, 64, 397.
51. R. Fletcher, Comput. J., 1970, 13, 317.
52. (a) S. L. Johnson, Adv. Phys. Org. Chem., 1967, 5, 237;
53. (b) W. P. Jencks, Catalysis in chemistry and enzymology, McGraw-Hill, New York, 1968, pp. 354-463;
54. (c) T. C. Bruice and S. J. Benkovic, Bioorganic mechanisms, vol. 1, W. A. Benjamin, Inc., New York, 1966, pp. 1-211;
55. (d) M. L. Bender, Chem. Rev., 1960, 60, 53; see also Mechanism of homogeneous catalysis from proton to proteins, Wiley, New York, 1971, p. 108;
56. (d) M. L. Bender, Chem. Rev., 1960, 60, 53; see also Mechanism of homogeneous catalysis from proton to proteins, Wiley, New York, 1971, p. 108;
57. (e) B. Capon, A. K. Ghosh and D. McL. A. Grieve, Acc. Chem. Res., 1981, 14, 306.
58. D. J. Martin and C. E. Griffin, J. Org. Chem., 1965, 30, 4034.
59. L. T. Kanerva and E. K. Euranto, J. Chem. Soc., Perkin Trans 2, 1987, 441.
60. H. Dahn, P. Pechy and V. V. Toan, Magn. Reson. Chem., 1990, 28, 883.
61. H. Duddeck and R. Lecht, Phosphorus and Sulfur, 1987, 29, 169.
62. T. Fujita and T. Nishioka, Progress in physical organic chemistry, ed. R. W. Taft, Wiley, New York, 1976, 12, 49.
63. J. Hine and G. F. Koser, J. Org. Chem., 1971, 36, 1348.
64. L. H. Funderburk, L. Aldwin and W. P. Jencks, J. Am. Chem. Soc., 1978, 98, 5444.
65. (a) J. L. Palmer and W. P. Jencks, J. Am. Chem. Soc., 1980, 102, 6472;
66. (b) P. E. Sorensen and W. P. Jencks, J. Am. Chem. Soc., 1987, 109, 4675;
67. (b) P. E. Sorensen, K. J. Pedersen, P. R. Pedersen, V. M. Kanacasabapapathy and R. A. McClelland, J. Am. Chem. Soc., 1988, 110, 5118.
68. C. A. Coleman and C. J. Murry, J. Am. Chem. Soc., 1991, 113, 1677.
69. B. Capon, M. I. Dosunmu and M. de N. de Matos Sanchez, Adv. Phys. Org. Chem., 1985, 21, 37.
70. (a) J. M. Sayer and W. P. Jencks, J. Am. Chem. Soc., 1973, 95, 5637;
71. (b) H. Fischer, F. X. DeCandis, S. D. Ogden and W. P. Jencks, J. Am. Chem. Soc., 1980, 102, 1340.
72. J. P. Fox, M. I. Page, A. Satterthwait and W. P. Jencks, J. Am. Chem. Soc., 1972, 94, 4731.
73. I. H. Williams, J. Am. Chem. Soc., 1987, 109, 6299.
74. 2O) = 3.6-5.3. D. Stefanidis and W. P. Jencks, J. Am. Chem. Soc., 1993, 115, 6045.
75. K. Bowden, Adv. Phys. Org. Chem., 1993, 28, 171.
76. H. Neuvonen, J. Chem. Soc., Perkin Trans. 2, 1990, 669.
77. C. Reichardt, Solvents and Solvent Effects in Organic Chemistry, VCH, Weinheim, 2nd edn., 1988, p. 408.
78. L. T. Kanerva, J. Chem. Soc., Perkin Trans. 2, 1986, 1433.
79. H. Neuvonen, J. Chem. Soc., Perkin Trans. 2, 1986, 1141.
80. P. Greenzaid, Z. Luz and D. Samuel, J. Am. Chem. Soc., 1967, 89, 749.
81. J. Fastrez, J. Am. Chem., Soc., 1977, 99, 7004.
82. J. P. Guthrie, Can. J. Chem., 1975, 53, 898.
83. M. R. Crampton, J. Chem. Soc., Perkin Trans. 2, 1975, 185.
84. D. L. Leussing, J. Org. Chem., 1990, 55, 666.