Syntheses, conformations, and basicities of bicyclic triamines

Journal of the American Chemical Society

Volumn 125, Issue 40, 2003, Pages 12196-12210

  Bell, Thomas W ^a   Choi, Heung Jin ^b,d   Harte, William ^b   Drew, Michael G B ^c  

^a UNIVERSITY OF NEVADA   (United States)

^b STONY BROOK UNIVERSITY   (United States)

^c UNIVERSITY OF READING   (United Kingdom)

^d Kyungpook National University   (South Korea)

Author keywords

[No Author keywords available]

Indexed keywords

ALKALINITY; CONFORMATIONS; CRYSTAL STRUCTURE; HYDROGEN BONDS; NUCLEAR MAGNETIC RESONANCE SPECTROSCOPY; SYNTHESIS (CHEMICAL); X RAY CRYSTALLOGRAPHY;

PROTONATION;

AMINES;

1,5,9 TRIAZABICYCLO[7.3.3]PENTADECANE; 1,5,9 TRIAZABICYCLO[9.1.1]TRIDECANE; 1,5,9 TRIAZACYCLODODECANE; 11 METHYLENE 1,5,9 TRIAZABICYCLO[7.3.3]PENTADECANE; 5 METHYL 1,5,9 TRIAZABICYCLO[7.3.3]PENTADECANE; 5 METHYL 11 METHYLENE 1,5,9 TRIAZABICYCLO[7.3.3]PENTADECANE; 7 METHYL 1,5,9 TRIAZABICYCLO[5.5.0]DODECANE; BICYCLO COMPOUND; CARBON; DODECANE; NITROGEN; POLYAMINE; PROTON; TRIAMINE; UNCLASSIFIED DRUG;

ACIDITY; ARTICLE; CALCULATION; CARBON NUCLEAR MAGNETIC RESONANCE; CHEMICAL BOND; CONFORMATION; CRYSTAL STRUCTURE; ENERGY; ENTHALPY; GAS; HYDROGEN BOND; HYPOTHESIS; PROTON NUCLEAR MAGNETIC RESONANCE; PROTON TRANSPORT; STRUCTURE ANALYSIS; SYNTHESIS; TEMPERATURE; THERMOSTABILITY; X RAY CRYSTALLOGRAPHY;

EID: 0141992302     PISSN: 00027863     EISSN: None     Source Type: Journal    
DOI: 10.1021/ja030236d     Document Type: Article

References (104)

1. (a) Staab, H. A.; Saupe, T. Angew. Chem., Int. Ed. Engl. 1988, 27, 865-879.
2. (b) Alder, R. W. Chem. Rev. 1989, 89, 1215-1223.
3. (c) Bencini, A.; Bianchi, A.; Garcia-España, E.; Micheloni, M.; Ramirez, J. A. Coord. Chem. Rev. 1999, 188, 97-156.
4. (a) Alder, R. W.; Bowman, P. S.; Steele, W. R. S.; Winterman, D. R. J. Chem. Soc. Chem. Commun. 1968, 723-724.
5. (b) Hibbert, F.; Hunte, K. P. P. J. Chem. Soc., Perkin Trans. 2 1981, 1562-1565.
6. (c) Hibbert, F.; Hunte, K. P. P. J. Chem Soc., Perkin. Trans. 2 1983, 1895-1899.
7. (d) Sjemik-Hojniak, A.; Zwier, J. M.; Buma, W. J.; Bursi, R.; van der Waals, J. H. J. Am. Chem. Soc. 1998, 120, 4840-4844.
8. (e) Wozniak, K.; Raczynska, E. D.; Korybut-Daszkiewicz, B. Isr. J. Chem. 1999, 39, 245-252.
9. (f) Pietrzak, M.; Stefaniak, L.; Pozharskii, A. F.; Ozeryanskii, V. A.; Nowicka-Scheibe, J.; Grech, E.; Webb, G. A. J. Phys. Org. Chem. 2000, 13, 35-38.
10. (g) Alkorta, I.; Elguero, J. Struct. Chem. 2000, 11, 335-340.
11. (h) Guo, H.; Salahub, D. R. THEOCHEM 2001, 547, 113-118.
12. Schwesinger, R.; Missfeldt, M.; Peters, K.; von Schnering, H. G. Angew. Chem., Int. Ed. Engl. 1987, 26, 1165-1167.
13. For example: (a) Zirnstein, M. A.; Staab, H. A. Angew. Chem., Int. Ed. Engl. 1987, 26, 460-461.
14. (b) Krieger, C.; Newsom, I.; Zirnstein, M. A.; Staab, H. A. Angew. Chem., Int. Ed. Engl. 1989, 28, 84-86.
15. (c) Staab, H. A.; Zirnstein, M. A.; Krieger, C. Angew. Chem. Int. Ed. Engl. 1989, 28, 86-88.
16. (d) Brzezinski, B.; Glowiak, T.; Grech, E.; Malarski, Z.; Sobczyk, L. J. Chem. Soc., Perkin Trans. 2 1991, 1643-1647.
17. (e) Pozharskii, A. F.; Chikina, N. L.; Vistorobskii, N. V.; Ozeryanskii, V. A. Russ. J. Org. Chem. 1997, 33, 1727-1730.
18. (f) Howard, S. T.; Platts, J. A. J. Org. Chem. 1998, 63, 3568-3571.
19. (g) Howard, S. T.; Fallis, I. A. J. Org. Chem. 1998, 63, 7117-7119.
20. (h) Staab, H. A.; Elbl-Weiser, K.; Krieger, C. Eur. J. Org. Chem. 2000, 327-333.
21. (i) Staab, H. A.; Kirsch, A.; Barth, T.; Krieger, C.; Neugebauer, F. A. Eur. J. Org. Chem. 2000, 1617-1622.
22. (j) Ozeryanskii, V. A.; Pozharskii, A. F.; Milgizina, G. R.; Howard, S. T. J. Org. Chem. 2000, 65, 7707-7709.
23. (k) Howard, S. T. J. Am. Chem. Soc. 2000, 122, 8238-8244.
24. (l) Mascal, M.; Lera, M.; Blake, A. J.; Czaja, M.; Kozak, A.; Makowski, M.; Chmurzynski, L. Angew. Chem., Int. Ed. 2001, 40, 3696-3698.
25. (m) Perrin, C. L.; Ohta, B. K. J. Am. Chem. Soc. 2001, 123, 6520-6526.
26. (n) Pozharskii, A. F.; Ozeryanskii, V. A.; Starikova, Z. A. J. Chem. Soc., Perkin Trans. 2 2002, 318-322.
27. (o) Howard, S. T.; Platts, J. A.; Coogan, M. P. J. Chem. Soc., Perkin Trans. 2 2002, 899-905.
28. (p) Raab, V.; Kipke, J.; Gschwind, R. M.; Sundermeyer, J. Chem. Eur. J. 2002, 8, 1682-1693.
29. (a) Alder, R. W. Acc. Chem. Res. 1983, 16, 321-327.
30. (b) Alder, R. W.; East, S. P. Chem. Rev. 1996, 96, 2097-2111.
31. (a) Alder, R. W.; Orpen, A. G.; Sessions, R. B. J. Chem. Soc., Chem. Commun. 1983, 999-1000.
32. (b) Alder, R. W.; Moss, R. E.; Sessions, R. B. J. Chem. Soc., Chem. Commun. 1983, 1000-1002.
33. (a) Gerlt, J. A.; Gassman, P. G. J. Am. Chem. Soc. 1993, 115, 11552-11568.
34. (b) Cleland, W. W.; Kreevoy, M. M. Science 1994, 264, 1887-1890.
35. (c) Shan, S.; Loh, S.; Herschlag, D. Science 1996, 272, 97-101.
36. (d) Ash, E. L.; Sudmeier, J. L.; De Fabo, E. C.; Bachovchin, W. W. Science 1997, 278, 1128-1132.
37. (e) Perrin, C. L.; Nielson, J. B. Annu. Rev. Phys. Chem. 1997, 48, 511-544.
38. (f) Kumar, G. A.; McAllister, M. A. J. Am. Chem. Soc. 1998, 120, 3159-3165.
39. (g) Cleland, W. W. Arch. Biochem. Biophys. 2000, 382, 1-5.
40. (h) Horsewill, A. J.; Jones, N. H.; Caciuffo, R. Science 2001, 291, 100-103.
41. (i) Ghosh, A.; Moulder, J.; Broring, M.; Vogel, E. Angew. Chem., Int. Ed. 2001, 40, 431-434.
42. (j) Mock, W. L.; Morsch, L. A. Tetrahedron 2001, 57, 2957-2964.
43. (k) Filarowski, A.; Koll, A.; Glowiak, T. J. Chem. Soc., Perkin Trans. 2 2002, 835-842.
44. (a) Koyama, H.; Yoshino, T. Bull. Chem. Soc. Jpn. 1972, 45, 481-484.
45. (b) Riedo, T. J.; Kaden, T. A. Chimia 1977, 31, 220-222.
46. (c) Zompa, L. J. Inorg. Chem. 1978, 17, 2531-2536.
47. (d) Riedo, T. J.; Kaden, T. A. Helv. Chim. Acta 1979, 62, 1089-1096.
48. (e) Briellmann, M.; Kaderli, S.; Meyer, C. J.; Zuberbühler, A. D. Helv. Chim. Acta 1987, 70, 680-689.
49. (f) Geraldes, C. F. G. C.; Sherry, A. D.; Marques, M. P. M.; Alpoim, M. C.; Cortes, S. J. Chem. Soc., Perkin Trans. 2 1991, 137-146.
50. (a) Bell, T. W.; Choi, H.-J.; Harte, W. J. Am. Chem. Soc. 1986, 108, 7427-7428.
51. (b) Harte, W. E. M.S. Thesis, State University of New York at Stony Brook, NY, 1985.
52. (c) Choi, H.-J. Ph.D. Thesis, State University of New York at Stony Brook, NY, 1989.
53. (a) Bianchi, A.; Ciampolini, M.; Micheloni, M.; Nardi, N.; Valtancoli, B.; Mangani, S.; García-España, E.; Ramírez, J. A. J. Chem Soc., Perkin Trans. 2 1989, 1131-1137.
54. (b) Weismam, G. R.; Rogers, M. E.; Wong, E. H.; Jasinski, J. P.; Paight, E. S. J. Am. Chem. Soc. 1990, 112, 8604-8605.
55. (c) Wong, E. H.; Weisman, G. R.; Hill, D. C.; Reed, D. P.; Rogers, M. E. ; Condon, J. S.; Fagan, M. A.; Calabrese, J. C.; Lam, K.-C.; Guzei, I. A.; Rheingold, A. L. J. Am. Chem. Soc. 2000, 122, 10561-10572.
56. (a) Ciampolini, M.; Micheloni, M.; Vizza, F.; Zanobini, F.; Chimichi, S. ; Dapporto, P. J. Chem. Soc., Dalton Trans. 1986, 505-518.
57. (b) Ciampolini, M.; Micheloni, M.; Orioli, P.; Vizza, F.; Mangani, S.; Zanobini, F. Gazz. Chim. Ital. 1986, 116, 189-192.
58. (c) Micheloni, M. J. Coord. Chem. 1988, 18, 3-19.
59. Smith, P. B.; Dye, J. L.; Cheney, J.; Lehn, J.-M. J. Am. Chem. Soc. 1981, 103, 6044-6048.
60. (a) Kemp, D. S.; Punzar, R. V.; Chabala, J. C. Tetrahedron Lett. 1978, 6, 547-550.
61. (b) Kemp, D. S.; Sidell, M. D.; Shortridge, T. J. J. Org. Chem. 1979, 44. 4473-4476.
62. (a) Bencini, A.; Bianchi, A.; Ciampolini, M.; Garcia-España, E.; Dapporto, P.; Micheloni, M.; Paoli, P.; Ramirez, J. A.; Valtancoli, B. J. Chem. Soc., Chem. Commun. 1989, 701-703.
63. (b) Bencini, A.; Bianchi, A.; Borselli, A.; Ciampolini, M.; Micheloni, M.; Nardi, N.; Paoli, P.; Valtancoli, B.; Chimichi, S.; Dapporto, P. J. Chem. Soc., Chem. Commun. 1990, 174-175.
64. (c) Bencini, A.; Bianchi, A.; Borselli, A.; Chimichi, S.; Ciampolini, M. ; Dapporto, P.; Micheloni, M.; Nardi, N.; Paoli, P.; Valtancoli, B. J. Am. Chem. Soc. 1990, 29, 3282-3286.
65. (d) Bencini, A.; Bianchi, A.; Chimichi, S.; Ciampolini, M.; Dapporto, P. ; García-España, E.; Micheloni, M.; Nardi, N.; Paoli, P.; Valtancoli, B. J. Am. Chem. Soc. 1991, 30, 3687-3691.
66. (a) Richman, J.; Atkins, T. J. J. Am. Chem. Soc. 1974, 96, 2268-2270.
67. (b) Atkins, T. J.; Richman, J. E.; Oettle, W. F. Organic Syntheses; Wiley: New York, 1988; Collect. Vol. 6; pp 652-662.
68. (a) Nelson, E. R.; Maienthal, M.; Lane, L. A.; Benderley, A. A. J. Am. Chem. Soc. 1957, 79, 3467-3469.
69. (b) Smith, W. L.; Ekstrand, J. D.; Raymond, K. N. J. Am. Chem. Soc. 1978, 100, 3539-3544.
70. (a) Deronde, M.; Driscoll, D.; Yang, R.; Zompa, L. J. Inorg. Nucl. Chem. Lett. 1975, 11, 521-528.
71. (b) Yang, R.; Zompa, L. J. Inorg. Chem. 1976, 15, 1499-1502.
72. (c) Chavez, F.; Sherry, A. D. J. Org. Chem. 1989, 54, 2990-2992.
73. (a) Clarke, T. H.; Gillespie, H. B.; Weisshaus, S. Z. J. Am. Chem. Soc. 1933, 55, 4571-4587.
74. (b) Pine, S. H.; Sanchez, B. L. J. Org. Chem. 1971, 36, 829-832.
75. (a) Borch, R. F.; Hassid, A. I. J. Org. Chem. 1972, 37, 1673-1674.
76. (b) Jentoft, N.; Dearborn, D. G. J. Biol. Chem. 1979, 254, 4359-4365.
77. Schulze, K.; Winkler, G.; Dietrich, W.; Mühlstädt, M. J. Prakt. Chem. 1977, 319, 463-474.
78. (a) Schlessinger, R. H.; Ponticello, G. S. Tetrahedron Lett. 1969, 4361-4364.
79. (b) Baldwin, J. J.; Raab, A. W.; Mensler, K.; Arison, B. H.; McClure, D. E. J. Org. Chem. 1978, 43, 4876-4878.
80. (a) Bergeron, R. J.; Garlich, J. R. Synthesis 1984, 782-784.
81. (b) Bergeron, R. J.; Kline, S. J.; Stolowich, N. J.; McGovern, K. A.; Burton, P. S. J. Org. Chem. 1981, 46, 4524-4529.
82. (c) Bergeron, R. J.; Burton, P. S.; McGovern, K. A.; Kline, S. J. Synthesis 1981, 732-733.
83. Mikolajewska, H.; Kotelko, A. Acta Pol. Pharm. 1966. 23, 425-431.
84. ElAmin, B.; Anantharamaiah, G. A.; Royer, G. P.; Means, G. E. J. Org. Chem. 1979, 44, 3442-3444.
85. (a) Olofsen, R. A.; Martz, J. T.; Senet, J.-P.; Piteau, M.; Malfroot, T. J. Org. Chem. 1984, 49, 2081-2082.
86. (b) Olofsen, R. A.; Abbott, D. E. J. Org. Chem. 1984, 49, 2795-2799.
87. Hamer, J.; Macaluso, A. Chem. Rev. 1964, 473-495.
88. (a) Barluenga, J.; Fañanás, F. J.; Villamaña, J.; Yus, M. J. Org. Chem. 1982, 47, 1560-1564.
89. (b) Tong, M. K.; Blumenthal, E. M.; Ganem, B. Tetrahedron Lett. 1990, 31, 1683-1684.
90. Schaeffer, G. W.; Anderson, E. R. J. Am. Chem. Soc. 1949, 71, 2143-2145.
91. (a) Ebnöther, A.; Jucker, E. Helv. Chim. Acta 1964, 47, 745-756.
92. (b) Hammer, C. F.; Heller, S. R. J. Chem. Soc., Chem. Commun. 1966, 919-920.
93. Weisman, G. R.; Johnson. V.; Fiala, R. E. Tetrahedron Lett. 1980, 21, 3635-3638.
94. 13C NMR spectrum, even down to -40°C.
95. Lambert, J. B. In Topics in Stereochemistry; Allinger, N. E., Eliel, E. L., Eds.: Wiley-Interscience: NY, 1975; Vol. 6, pp 19-105.
96. Bianchi, A.; Ciampolini, M.; Micheloni, M.; Chimichi, S.; Zanobini, F. Gazz. Chim. Ital. 1987, 117, 499-502.
97. Albert, A.; Serjeant, E. P. The Determination of Ionization Constants: A Laboratory, Manual; Chapman and Hall: London, 1984.
98. Walker, N.; Stuart, D. Acta Crystallgr., Sect. A 1983, 39. 158.
99. Shelx76 Package for Crystal Stucture Determination, G. M. Sheldrick, University of Cambridge, 1976.
100. Allinger, N. L.; Yuh, Y. H., MM2 Q.C.P.E. Program No. 423, Quantum Chemistry Program Exchange, Indiana University Chemistry Department, Indiana, U.S.A., Modified Version of 1987.
101. Allinger, N. L.; Kok, R. A.; Iman, M. R. J. Comput. Chem. 1988, 9, 591.
102. Frisch, M. J.; Trucks, G. W.; Schlegel, H. B.; Scuseria, G. E.; Robb, M. A.; Cheeseman, J. R.; Zakrzewski, V. G.; Montogomery, J. A.; Stratman, R. E.; Burant, J. C.; Dapprich, S.; Millam, J. M.; Daniels, A. D.; Kudin, K. N.; Strain, M. C.; Farkas, O.; Tomasi, J.; Barone, V.; Cossi, M.; Cammi, R.; Mennucci, B.; Pomelli, C.; Adamo, C.; Clifford, S.; Ochterski, J.; Petersson, G. A.; Ayala, P. Y.; Cui, Q.; Morokuma, K.; Malick, D. K.; Rabuck, A. D.; Raghavachari, K.; Foresman, J. B.; Cioslowski, J.; Ortiz, J. V.; Stefanov, B. B.; Liu, G.; Liashenko, A.; Piskorz, P.; Komaromi, I.; Gomperts, R.; Martin, R. L.; Fox, D. J.; Keith, T.; Al-Latham, M. A.; Peng, C. Y.; Nanayakkara, A.; Gonzalez, C.; Challacombe, M.; Gill, P. M. W.; Johnson, B.; Chen, W.; Wong, M. W.; Andres, J. L.; Head-Gordon, M.; Replogle E. S.; Pople, J. A. Gaussian98; Gaussian, Inc.: Pittsburgh, PA, 1998.
103. General Electric Company, Manual for NMC 300 NMR Spectrometer.
104. Sandström, J. Dynamic NMR Spectroscopy; Academic Press: New York, 1982; pp 77-123.