Rates and equilibria of the reactions of tertiary phosphanes and phosphites with benzhydrylium ions

Chemistry - A European Journal

Volumn 11, Issue 3, 2005, Pages 917-927

  Kempf, Bernhard ^a   Mayr, Herbert ^a  

^a UNIVERSITY OF MUNICH   (Germany)

Author keywords

Carbocations; Intrinsic barriers; Kinetics; Phosphites; Tertiary phosphanes

Indexed keywords

PHOSPHATES; PHOTOMETRY; RATE CONSTANTS; REACTION KINETICS;

ELECTROPHILES; NUCLEOPHILICITY; TERTIARY PHOSPHANES;

AROMATIC HYDROCARBONS;

BENZHYDRYL DERIVATIVE; PHOSPHITE; PHOSPHONIUM DERIVATIVE; PHOSPHORUS DERIVATIVE; QUINONE DERIVATIVE; TERTIARY PHOSPHANE; UNCLASSIFIED DRUG;

ARTICLE; CATALYSIS; CHEMICAL REACTION KINETICS; EQUILIBRIUM CONSTANT; PHOTOMETRY; PKA;

BENZHYDRYL COMPOUNDS; INDOLEQUINONES; KINETICS; LIGANDS; MOLECULAR STRUCTURE; PHOSPHINES; PHOSPHITES;

EID: 13244260768     PISSN: 09476539     EISSN: None     Source Type: Journal    
DOI: 10.1002/chem.200400696     Document Type: Article

References (85)

1. a) C. A. Tolman, J. Am. Chem. Soc. 1970, 92, 2953-2956;
2. b) C. A. Tolman, J. Am. Chem. Soc. 1970, 92, 2956-2965;
3. c) C. A. Tolman, Chem. Rev. 1977, 77, 313-348.
4. D. Basavaiah, A. J. Rao, T. Satyanarayana, Chem. Rev. 2003, 103, 811-891.
5. I. C. Stewart, R. G. Bergman, F. D. Toste, J. Am. Chem. Soc. 2003, 125, 8696-8697.
6. a) L.-C. Wang, A.-L. Luis, K. Agapiou, H.-Y. Jang, M. J. Krische, J. Am. Chem. Soc. 2002, 124, 2402-2403;
7. b) S. A. Frank, D. J. Mergott, W. R. Roush, J. Am. Chem. Soc. 2002, 124, 2404-2405.
8. a) B. M. Trost, U. Kazmaier, J. Am. Chem. Soc. 1992, 114, 7933-7935;
9. b) C. Guo, X. Lu, J. Chem. Soc. Perkin Trans, 1 1993, 1921-1923.
10. a) B. M. Trost, G. R. Dake, J. Org. Chem. 1997, 62, 5670-5671;
11. b) B. M. Trost, G. R. Dake, J. Am. Chem. Soc. 1997, 119, 7595-7596.
12. a) C. Zhang, X. Lu, J. Org. Chem. 1995, 60, 2906-2908;
13. b) G. Zhu, Z. Chen, Q. Jiang, D. Xiao, P. Cao, X. Zhang, J. Am. Chem. Soc. 1997, 119, 3836-3837;
14. c) Z. Xu, X. Lu, J. Org. Chem. 1998, 63, 5031-5041;
15. d) Y. Du, X. Lu, Y. Yu, J. Org. Chem. 2002, 67, 8901-1905;
16. e) J.-C. Wang, S.-S. Ng, M. J. Krische, J. Am. Chem. Soc. 2003, 125, 3682-3683.
17. X.-F. Zhu, J. Lan, O. Kwon, J. Am. Chem. Soc. 2003, 125, 4716-4717.
18. C. Cho, J.-R. Kong, M. J. Krische, Org. Lett. 2004, 6, 1337-1339.
19. H. Mayr, T. Bug, M. F. Gotta, N. Hering, B. Irrgang, B. Janker, B. Kempf, R. Loos, A. R. Ofial, G. Remennikov, H. Schimmel, J. Am. Chem. Soc. 2001, 123, 9500-9512.
20. a) H. Mayr, M. Patz, Angew. Chem. 1994, 106, 990-1010; Angew. Chem. Int. Ed. Engl. 1994, 33, 938-957;
21. a) H. Mayr, M. Patz, Angew. Chem. 1994, 106, 990-1010; Angew. Chem. Int. Ed. Engl. 1994, 33, 938-957;
22. b) H. Mayr, M. Patz, M. F. Gotta, A. R. Ofial, Pure Appl. Chem. 1998, 70, 1993-2000;
23. c) H. Mayr, O. Kuhn, M. F. Gotta, M. Patz, J. Phys. Org. Chem. 1998, 11, 642-654.
24. For a review on π nucleophilicity, see: H. Mayr, B. Kempf, A. R. Ofial, Acc. Chem. Res. 2003, 36, 66-77.
25. For reactivities of enamines. see: B. Kempf, N. Hampel, A. R. Ofial, H. Mayr, Chem. Eur. J. 2003, 9, 2209-2218.
26. For reactivities of diazo compounds, see: T. Bug, M. Hartnagel, C. Schlierf, H. Mayr, Chem. Eur. J. 2003, 9, 4068-4076.
27. For reactivities of carbanions, see: a) T. Bug, H. Mayr, J. Am. Chem. Soc. 2003, 125, 12980-12986;
28. b) R. Lucius, R. Loos, H. Mayr, Angew. Chem. 2002, 114, 97-102; Angew. Chem. Int. Ed. 2002, 41, 91-95;
29. b) R. Lucius, R. Loos, H. Mayr, Angew. Chem. 2002, 114, 97-102; Angew. Chem. Int. Ed. 2002, 41, 91-95;
30. c) R. Lucius, H. Mayr, Angew. Chem. 2000, 112, 2086-2089; Angew. Chem. Int. Ed. 2000, 39, 1995-1997;
31. c) R. Lucius, H. Mayr, Angew. Chem. 2000, 112, 2086-2089; Angew. Chem. Int. Ed. 2000, 39, 1995-1997;
32. d) T. Bug, T. Lemek, H. Mayr, J. Org. Chem. 2004, 69, 7565-7576.
33. For reactivities of hydride donors, see: a) M.-A. Funke, H. Mayr, Chem. Eur. J. 1997, 3, 1214-1222;
34. b) see ref. [10];
35. c) H. Mayr, G. Lang, A. R. Ofial, J. Am. Chem. Soc. 2002, 124, 4076-4083.
36. a) S. Minegishi, H. Mayr, J. Am, Chem. Soc. 2003, 125, 286-295;
37. b) R. Loos, S. Kobayashi, H. Mayr, J. Am. Chem. Soc. 2003, 125, 14126-14132.
38. a) C. Schindele, K. N. Houk, H. Mayr, J. Am. Chem. Soc. 2002, 124, 11208-11214;
39. b) H. Mayr, A. R. Ofial in Carbocation Chemistry (Eds.: G. A. Olah, G. K. S. Prakash), Wiley, Hoboken, NJ, 2004, Chapt. 13, pp. 331-338.
40. O. Exner, Correlation Analysis of Chemical Data, Plenum Press, New York, 1988.
41. T. Allman, R. G. Goel, Can. J. Chem. 1982, 60, 716-722.
42. L. A. P. Kane-Maguire, M. Manthey, J. G. Alton, G. R. John, Inorg. Chim. Acta 1995, 240, 71-79.
43. H. Mayr, R. Schneider, C. Schade, J. Bartl, R. Bederke, J. Am. Chem. Soc. 1990, 112, 4446-4454.
44. R. Schmid, V. N. Sapunov, Nonformal Kinetics, Verlag Chemie, Weinheim, 1981.
45. R. Lucius, H. Mayr, unpublished results.
46. T. Bug, Dissertation, Ludwig-Maximilians-Universität München, 2003.
47. H. Schimmel, Dissertation, Ludwig-Maximilians-Universität München, 2000.
48. B. Irrgang, H. Mayr, unpublished results.
49. R. Loos, Dissertation, Ludwig-Maximilians-Universität München, 2003.
50. N. Hering, Diplomarbeit, Technische Hochschule Darmstadt, 1996.
51. G. Hagen, H. Mayr, J. Am. Chem. Soc. 1991, 113, 4954-4961.
52. H. Mayr, N. Basso, G. Hagen, J. Am. Chem. Soc. 1992, 114, 3060-3066.
53. C. Reichardt, Solvents and Solvent Effects in Organic Chemistry. 3rd ed., Wiley-VCH, Weinheim, 2003.
54. G. Gardaci, S. M. Murgia, A, Foffani, J. Organomet. Chem. 1970, 23, 265-273.
55. L. A. P. Kane-Maguire, E. D. Honig, D. A. Sweigart, Chem. Rev. 1984, 84, 525-543.
56. L. A. P. Kane-Maguire, J. Chem. Soc. Dalton Trans. 1979, 873-878.
57. T. J. Alavosus, D. A. Sweigart, J. Am. Chem. Soc. 1985, 107, 985-987.
58. a) J. E. Leffler, E. Grunwald, Rates and Equilibria of Organic Reactions, Wiley, New York, 1963;
59. b) N. B. Chapman, J. Shorter, Advances in Linear Free Energy Relationships, Plenum Press, London, 1972.
60. a) A. Williams, Adv. Phys. Org. Chem. 1992, 27, 1-55;
61. b) A. Williams, Free Energy Relationships in Organic and Bio-organic Chemistry, The Royal Society of Chemistry, Cambridge, 2003.
62. a) C. F. Bernasconi, G. D. Leonarduzzi, J. Am. Chem. Soc. 1982, 104, 5133-5142;
63. b) E. M. Arnett, R. Reich, J. Am. Chem. Soc. 1980, 102, 5892-5902;
64. c) C. F. Bernasconi, R. B. Killion, J. Am. Chem. Soc. 1988, 110, 7506-7512;
65. d) J. E. Dixon, T. C. Bruice, J. Am. Chem. Soc. 1971, 93, 3248-3254.
66. a) R. A. Marcus, J. Am. Chem. Soc. 1969, 91, 7224-7225;
67. b) I. S. Han Lee, E. H. Jeoung, M. Kreevoy, J. Am. Chem. Soc. 1997, 119, 2722-2728;
68. c) M. Kreevoy, I.-S. Han Lee, J. Am. Chem. Soc. 1984, 106, 2550-2553.
69. R. A. Marcus, J. Phys. Chem. 1968, 72, 891-899.
70. E.-U. Würthwein, G. Lang, L. H. Schappele, H. Mayr, J. Am. Chem. Soc. 2002, 124, 4084-4092.
71. A. S. Romakhin, E. V. Nikitin, O. V. Parakin, Yu, A, Ignat'ev, B. S. Mironov, Yu. M. Kargin, Zh. Obshch. Khim. 1986, 56, 2597-2601; J. Gen. Chem. USSR 1986, 56, 2298-2301.
72. A. S. Romakhin, E. V. Nikitin, O. V. Parakin, Yu, A, Ignat'ev, B. S. Mironov, Yu. M. Kargin, Zh. Obshch. Khim. 1986, 56, 2597-2601; J. Gen. Chem. USSR 1986, 56, 2298-2301.
73. Yu. M. Kargin, Yu. G. Budnikova, Russ. J. Gen. Chem. 2001, 71, 1393-1421; Zh. Obshch. Khim. 2001, 71, 1472-1502.
74. Yu. M. Kargin, Yu. G. Budnikova, Russ. J. Gen. Chem. 2001, 71, 1393-1421; Zh. Obshch. Khim. 2001, 71, 1472-1502.
75. A. R. Ofial, K. Ohkubo, S. Fukuzumi, R. Lucius, H. Mayr, J. Am. Chem. Soc. 2003, 125, 10906-10912.
76. M. Patz, H. Mayr, J. Maruta, S. Fukuzumi, Angew. Chem. 1995, 107, 1351-1353; Angew. Chem. Int. Ed. Engl. 1995, 34, 1222-1225.
77. M. Patz, H. Mayr, J. Maruta, S. Fukuzumi, Angew. Chem. 1995, 107, 1351-1353; Angew. Chem. Int. Ed. Engl. 1995, 34, 1222-1225.
78. D. Woska, A. Frock, W. P. Giering, Organometallics 2000, 19, 4629-4638.
79. A. L. Fernandez, C. Reyes, A. Frock, W. P. Giering, J. Chem. Soc. Perkin Trans. 2 2000, 1033-1041.
80. We thank Prof. W. P. Giering for treating our data with the QALE procedure (see ref. [48]).
81. R. D. Pike, D. A. Sweigart, Coord. Chem. Rev. 1999, 187, 183-222.
82. a) C. D. Ritchie, Acc. Chem. Res. 1972, 5, 348-354;
83. b) C. D. Ritchie, J. Am. Chem. Soc. 1975, 97, 1170-1179.
84. H. Gilman, E. A. Zoellner, W. M. Selby, J. Am. Chem. Soc. 1933, 55, 1252-1257.
85. G. Tomaschewski, J. Prakt. Chem. 1966, 33, 168-177.