Effects of charge separation, effective concentration, and aggregate formation on the phase transfer catalyzed alkylation of phenol

Journal of the American Chemical Society

Volumn 134, Issue 32, 2012, Pages 13415-13429

  Denmark, Scott E ^a   Weintraub, Robert C ^a   Gould, Nathan D ^a  

^a UNIVERSITY OF ILLINOIS AT URBANA CHAMPAIGN   (United States)

Author keywords

[No Author keywords available]

Indexed keywords

AGGREGATE FORMATION; CHARGE SEPARATIONS; EFFECTIVE CONCENTRATION; EXTRACTION MECHANISMS; HOMOGENEOUS SOLUTIONS; INTRINSIC REACTIVITY; LIPOPHILICITY; N-BUTYL BROMIDES; ORGANIC PHASE; PHASE TRANSFER; PHASE TRANSFER CATALYSIS; POTASSIUM PHENOXIDE; PRIMARY FACTORS; QUATERNARY AMMONIUM BROMIDE; TETRAALKYLAMMONIUM;

ALKYLATION; BROMINE COMPOUNDS; CATALYSIS; CATALYST ACTIVITY; PHENOLS; STOICHIOMETRY;

AGGREGATES;

AMMONIA; BROMIDE; BUTANE; CATION; HEXANE; OCTANE; PHENOL; POTASSIUM;

ALKYLATION; ARTICLE; CATALYSIS; CHEMICAL REACTION; CONTROLLED STUDY; LIPOPHILICITY; STOICHIOMETRY; TITRIMETRY;

EID: 84865109294     PISSN: 00027863     EISSN: 15205126     Source Type: Journal    
DOI: 10.1021/ja304808u     Document Type: Article

References (106)

1. Anastas, P.; Warner, J. Green Chemistry: Theory and Practice; Oxford University Press: Oxford, UK, 1998.
2. Weber, W. P.; Gokel, G. W. Phase Transfer Catalysis in Organic Synthesis; Springer-Verlag: Berlin/New York, 1977; Vol. 4.
3. Dehmlow, E. V.; Dehmlow, S. S. Phase Transfer Catalysis; Verlag Chemie: Weinheim/Deerfield Beach, 1983; Vol. 11.
4. Phase-Transfer Catalysis: New Chemistry, Catalysts, and Applications; American Chemical Society: Washington, DC, 1985.
5. Starks, C. M.; Liotta, C. L.; Halpern, M. Phase-Transfer Catalysis: Fundamentals, Applications and Industrial Perspectives; Chapman and Hall: New York, 1994.
6. Phase-Transfer Catalysis: Mechanisms and Syntheses; Halpern, M. E., Ed.; American Chemical Society: Washington, DC, 1997.
7. Makosza, M.; Fedorynski, M. In Interfacial Catalysis; Volkov, A. G., Ed.; Marcel Dekker: New York, 2003; pp 150-201.
8. Handbook of Phase Transfer Catalysis; Sasson, Y., Neumann, R., Eds.; Chapman & Hall: London, 1997.
9. Jones, R. A. Quaternary Ammonium Salt: Their Use in Phase Transfer Catalysis; Academic Press: London, 2001.
10. Denmark, S. E.; Gould, N. D.; Wolf, L. M. J. Org. Chem. 2011, 76, 4337-4357
11. Denmark, S. E.; Gould, N. D.; Wolf, L. M. J. Org. Chem. 2011, 76, 4260-4336
12. Ionization Constants of Organic Acids in Solution; IUPAC Chemical Data Series No. 23, Sergent, E. P.; Dempsey, B., Eds.; Pergamon Press: Oxford, 1979.
13. Bordwell, F. G.; McCallum, R. J.; Olmstead, W. N. J. Org. Chem. 1984, 49, 1424-1427
14. Taft, R. W.; Bordwell, F. G. Acc. Chem. Res. 1988, 21, 463-469
15. Bordwell, F. G.; Harrelson, J. A. Can. J. Chem. 1990, 68, 1714-1718
16. Halpern, M. Phase Trans. Catal. Commun. 1995, 1, 1-3
17. Yang, H.-M.; Wu, H.-S. Catal. Rev. 2003, 45, 463-540
18. Rabinovitz, M.; Cohen, Y.; Halpern, M. Angew. Chem., Int. Ed. Engl. 1986, 25, 960-970
19. For the most recent summary of the state of mechanistic understanding of phase transfer catalysis, see: Makosza, M.; Fedorysnki, M. Catal. Rev. 2003, 45, 321-367
20. Starks, C. M.; Owens, R. M. J. Am. Chem. Soc. 1973, 95, 3613-3617
21. Wang, M.-L. In Handbook of Phase Transfer Catalysis; Sasson, Y.; Neumann, R., Eds.; Chapman & Hall: London, 1997; Chapter 2, pp 36-107.
22. Herriot, A. W.; Picker, D. Tetrahedron Lett. 1972, 13, 4521-4524
23. Gordon, J. E.; Kutina, R. E. J. Am. Chem. Soc. 1977, 99, 3903-3909
24. Herriot, A.; Picker, D. J. Am. Chem. Soc. 1975, 97, 2345-2349
25. Landini, D.; Maia, A.; Montanari, F. J. Am. Chem. Soc. 1978, 100, 2796-2801
26. Landini, D.; Maia, A.; Montanari, F. J. Chem. Soc., Chem. Commun. 1977, 112-113
27. Dehmlow, E. V. Angew. Chem., Int. Ed. Engl. 1977, 16, 493-505
28. Brändström, A. Adv. Phys. Org. Chem. 1977, 15, 267-330
29. Naik, S. D.; Doraiswamy, L. K. Am. Inst. Chem. Eng. J. 1998, 44, 612-646
30. Wang, M.-L.; Yang, H.-M. Chem. Eng. Sci. 1991, 46, 619-627
31. Wang, M.; Yang, H. Ind. Eng. Chem. Res. 1990, 29, 522-526
32. McKillop, A.; Fiaud, J.-C.; Hug, R. P. Tetrahedron 1974, 30, 1379-1382
33. Taft, R. W.; Bordwell, F. G. Acc. Chem. Res. 1988, 21, 463-469
34. Wang, D. H.; Weng, H. S. J. Chin. Inst. Chem. Eng. 1996, 27, 129-139
35. Weng, H. S.; Wang, D. H. J. Chin. Inst. Chem. Eng. 1996, 27, 419-426
36. Wang, D. H.; Weng, H. S. J. Chin. Inst. Chem. Eng. 1995, 26, 147-156
37. Wang, D. H.; Weng, H. S. J. Eng. Sci. 1995, 50, 3477
38. Yadav, G. D.; Desai, N. M. Org. Process Res. Dev. 2005, 9, 749-756
39. Makosza, M. Tetrahedron Lett. 1966, 7, 4261-4624
40. Makosza, M. Pure Appl. Chem. 1975, 43, 439-462
41. Makosza, M.; Bialecka, E. Tetrahedron Lett. 1977, 18, 183-186
42. Halpern, M.; Sasson, Y.; Willner, I.; Rabinovitz, M. Tetrahedron Lett. 1981, 22, 1719-1722
43. Halpern, M.; Sasson, Y.; Rabinovitz, M. J. Org. Chem. 1983, 48, 1022-1025
44. Halpern, M.; Sasson, Y.; Rabinovitz, M. J. Org. Chem. 1984, 49, 2011-2012
45. Halpern, M.; Feldman, D.; Sasson, Y.; Rabinovitz, M. Angew. Chem. 1984, 96, 79-80
46. Halpern, M.; Zahalaka, H. A.; Sasson, Y.; Rabinovitz, M. J. Org. Chem. 1985, 50, 5088-5092
47. Feldman, D.; Halpern, M.; Rabinovitz, M. J. Org. Chem. 1985, 50, 1746-1749
48. Synthetic and Natural Phenols; Tyman, J. H. P., Ed.; Elsevier: Amsterdam, 1996; Vol. 52.
49. Lewis, E. S.; Vanderpool, S. J. Am. Chem. Soc. 1977, 99, 1946-1949
50. For an overview and discussion of theoretical derivations of ammonium ion pair reactivity, see: Ions and Ion Pairs in Organic Reactions; Szwarc, M., Ed.; John Wiley & Sons: New York, 1974; Vols. 1 and 2.
51. Ugelstad, J.; Ellingsen, T.; Berge, A. Acta Chim. Scand 1966, 20, 1593-1598
52. Starks, C. M. In Phase-Transfer Catalysis; Halpern, M. E., Ed.; American Chemical Society: Washington, DC, 1997; Vol. 659, Chapter 2, pp 2-10.
53. Brändström, A.; Junggren, U. Acta Chem. Scand. 1969, 23, 2203-2204
54. Brändström, A; Junggren, U. Acta Chem. Scand. 1969, 23, 2204-2205
55. Brändström, A.; Junggren, U. Acta Chem. Scand. 1969, 23, 2536-2537
56. Brändström, A.; Junggren, U. Acta Chem. Scand. 1969, 23, 3585-3586
57. Brändström, A. Pure Appl. Chem. 1982, 54, 1769-1782
58. Wilson, K.; Adams, D. J.; Rothenberg, G.; Clark, J. H. J. Mol. Catal. A: Chem. 2000, 159, 309-314
59. Wang, M.-L. In Handbook of Phase Transfer Catalysis; Sasson, Y.; Neumann, R., Eds.; Chapman & Hall: London, 1997; Chapter 2, pp 36-107.
60. Wang, D.-H.; Weng, H.-S. Chem. Eng. Sci. 1988, 43, 2019-2024
61. Mason, D.; Magdassi, S.; Sasson, Y. J. Org. Chem. 1991, 56, 7229-7232
62. Bordwell, F. G.; Hughes, D. L. J. Org. Chem. 1982, 47, 3224-3232
63. Caulton, K. G.; Chisholm, M. H.; Drake, S. R.; Folting, K.; Huffman, J. C.; Streib, W. E. Inorg. Chem. 1993, 32, 1970-1976
64. Dinnebier, R. E.; Pink, M.; Sieler, J.; Norby, P.; Stephens, P. W. Inorg. Chem. 1998, 37, 4996-5000
65. Dinnebier, R. E.; Pink, M.; Sieler, J.; Stephens, P. W. Inorg. Chem. 1997, 36, 3398-3401
66. Fraser, M. E.; Fortier, S.; Markiewicz, M. K.; Rodrigue, A.; Bovenkamp, J. W. Can. J. Chem. 1987, 65, 2558-2563
67. Caulton, K. G.; Chisholm, M. H.; Drake, S. R.; Folting, K.; Huffman, J. C.; Streib, W. E. Inorg. Chem. 1993, 32, 1970-1976
68. Chantooni, M. K., Jr.; Kolthoff, I. M. J. Phys. Chem. 1976, 80, 1306-1310
69. Arnett, E. M.; Moriarity, T. C.; Small, L. E.; Rudolph, J. P.; Quirk, R. P. J. Am. Chem. Soc. 1973, 95, 1492-1495
70. Arnett, E. M.; Small, L. E.; Oancea, D.; Johnston, D. J. Am. Chem. Soc. 1976, 98, 7346-7350
71. Arnett, E. M.; Venkatasubramanium, K. G. J. Org. Chem. 1983, 48, 1569-1578
72. Silva, P. J. J. Org. Chem. 2009, 74, 914-916
73. Nielsen, M. F.; Hammerich, O. Acta Chem. Scand. 1989, 43, 269-274
74. Goddard, R.; Reetz, M.; Herzog, M. Tetrahedron 2002, 58, 7847-7850
75. Viout, P. J. Mol. Catal. 1981, 10, 231-240
76. Minot, C.; Trong, N. A. Tetrahedron Lett. 1975, 16, 3905-3908
77. Johnson, M. L.; Rodriguez, C.; Benjamin, I. J. Phys. Chem. A 2009, 113, 2086-2091
78. Nelson, K. V.; Benjamin, I. Chem. Phys. Lett. 2011, 508, 59-62
79. Nelson, K. V.; Benjamin, I. J. Phys. Chem. C 2010, 114, 1154-1163
80. Nelson, K. V.; Benjamin, I. J. Phys. Chem. C 2011, 115, 2290-2296
81. Pradines, V.; Poteau, R.; Pimienta, V. Eur. J. Chem Phys. Phys. Chem 2007, 8, 1524-1533
82. Coleman, M. T.; Leblanc, G. Org. Process Res. Dev. 2010, 14, 732-736
83. Harlow, G. A.; Noble, C. M.; Wyld, G. E. A. Anal. Chem. 1956, 28, 787-791
84. Abrams, I. M.; Millar, J. R. React. Funct. Polym. 1997, 35, 7-22
85. Section 6: Fluid Properties. CRC Handbook of Chemistry and Physics, 92 nd ed.; Haynes, W. M.; Lide, D. R., Eds.; CRC Press: Boca Raton, FL, 2011-2012; pp 212-228.
86. Hopkins, R. N.; Yerger, E. S.; Lynch, C. C. J. Am. Chem. Soc. 1939, 61, 2460-2461
87. Schneider, C. H.; Lynch, C. C. J. Am. Chem. Soc. 1943, 65, 1063-1066
88. 2O at 20 °C is 45.5 mM: Section 5: Aqueous Solubility and Henry's Law Constants of Organic Compounds. CRC Handbook of Chemistry and Physics, 92 nd ed.; Haynes, W. M.; Lide, D. R., Eds.; CRC Press: Boca Raton, FL, 2011-2012.
89. For a recent instructive analysis of nonlinear membrane permeability-lipophilicity models, see: Balaz, S. Chem. Rev. 2009, 109, 1793-1899
90. Anslyn, E. V.; Dougherty, D. Modern Physical Organic Chemistry; University Science Books: Sausalito, CA, 2006; Chapters 7-9.
91. Hansch, C. Acc. Chem. Res. 1969, 2, 232-239
92. Hansch, C.; Kurup, A.; Garg, R.; Gao, H. Chem. Rev. 2001, 101, 619-672
93. Sawada, K.; Chigira, F. J. Mol. Liq. 1995, 65/66, 265-268
94. Price, F. P., Jr.; Hammett, L. P. J. Am. Chem. Soc. 1941, 63, 2387-2393
95. Gustavii, K.; Schill, G. Acta Pharm. Suec 1966, 3, 241-258
96. Gustavii, K.; Schill, G. Acta Pharm. Suec 1966, 3, 259-268
97. Gustavii, K. Acta Pharm. Suec 1967, 4, 233-246
98. Burello, E.; Rothenberg, G. Int. J. Mol. Sci 2006, 7, 375-404
99. Maldonado, A. G.; Rothenberg, G. Chem. Soc. Rev. 2010, 39, 1891-1902
100. Buchwald, P. J. Pharm. Sci. 2005, 94, 2355-2379
101. Dehmlow, E. V.; Thieser, R.; Sasson, Y.; Pross, E. Tetrahedron 1985, 41, 2927-2932
102. Zerda, J.; Sasson, Y. J. Chem. Soc., Perkin Trans. 2 1987, 1147-1151
103. Such supramolecular structures have been identified for transport of hydrogen peroxide in ruthenium-catalyzed oxidations. Sasson et al. have identified the formation of vesicles as the mechanism of transport of hydrogen peroxide: Rothenberg, G.; Barak, G.; Sasson, Y. Tetrahedron 1999, 55, 6301-6310
104. Mason, D.; Magdassi, S.; Sasson, Y. J. Org. Chem. 1991, 56, 7229-7232
105. Wang, D.-H.; Weng, H.-S. Chem. Eng. Sci. 1995, 50, 3477-3486
106. Ma̧kosza, M.; Kryłowa, I. Tetrahedron 1999, 55, 6395-6402