Structural, vibrational, and electronic characteristics of enyne macrocycles as a function of ring strain

Journal of the American Chemical Society

Volumn 122, Issue 29, 2000, Pages 6917-6928

  Eisler, Sara ^a   McDonald, Robert ^a   Loppnow, Glen R ^a   Tykwinski, Rik R ^a  

^a UNIVERSITY OF ALBERTA   (Canada)

Author keywords

[No Author keywords available]

Indexed keywords

MACROCYCLIC COMPOUND;

ARTICLE; CARBON NUCLEAR MAGNETIC RESONANCE; CHEMICAL STRUCTURE; CONJUGATION; ENERGY TRANSFER; MOLECULAR DYNAMICS; RAMAN SPECTROMETRY; SYNTHESIS;

EID: 0034718066     PISSN: 00027863     EISSN: None     Source Type: Journal    
DOI: 10.1021/ja000617g     Document Type: Article

References (88)

1. Krebs, A.; Wilke, J. Top. Curr. Chem. 1983, 709, 189-233.
2. Blomquist, A. T.; Liu, L. H.; Bohrer, J. C. J. Am. Chem. Soc. 1952, 74, 3643-3647.
3. Blomquist, A. T.; Liu, L. H. J. Am. Chem. Soc. 1953, 75, 21532154.
4. Nicolaou, K. C.; Smith, A. L. In Modem Acetylene Chemistry', Stang, P. J., Diederich, F., Eds.; VCH: Weinheim, 1995; pp 203-283.
5. Modem Acetylene Chemistry; Stang, P. J., Deiderich, F., Eds.; VCH: Weinheim, 1995.
6. Carbon Rich Compounds II. Top. Curr. Chem. 1999, 201 (special issue).
7. Moore, J. S. Ace. Chem. Res. 1997, 30, 402-413.
8. (a) Tykwinski, R. R.; Diederich, F. Liebigs AnnJRecl. 1997, 649661.
9. (b) Diederich, F. Nature (London) 1994, 369, 199-207.
10. Diederich, F.; Rubin, Y. Angew. Chem., Int. Ed. Engl. 1992, 31, 1101-1123.
11. Sander, W. Angen: Chem., Im. Ed. Engl. 1994, 33, 1455-1456.
12. (a) Gleiter, R.; Schäfer, W. In The Chemistry of Triple-Bonded Functional Croups: Supplement C2; Patai, S., Ed.; John Wiley & Sons: Chichester, 1994; Vol. 2, pp 153-189.
13. (b) Gleiter, R. Angew. Chem., Int. Ed. Engl. 1992, 31, 27-44.
14. Nakagawa, M. In Tlie Chemistry of the Carbon-Carbon Triple Bond; Patai, S., Ed.; John Wiley & Sons: Chichester, 1978; pp 635-712.
15. Haley, M. M. Synlett 1998, 557-565.
16. Scott, L. T. PureAppL Chem. 1986, 58, 105-110.
17. Hoffmann, R. W. Dehydrobenzene and Cycloalkynes; Academic Press: New York, 1967.
18. Sakurai, H.; Nakadaira, Y.; Hosomi, A.; Eriyama, Y.; Kabuto, C. J. Am. Chem. Soc. 1983, 705, 3359-3360.
19. Rubin, Y. Chem. Eur. J. 1997, 3, 1009-1016.
20. Bunz, U. H. F.; Rubin, Y.; Tobe, Y. Chem. Soc. Rev. 1999, 107119.
21. (a) Meier, H.; Hanold, N.; Molz, T.; Bissinger, H. J.; Kolshorn, H.; Zountsas, J. Tetrahedron 1986, 42, 1711-1719.
22. (b) Meier, H.; Petersen, H.; Kolshorn, H. Chem. Ber. 1980, 113, 2398-2409.
23. Sondheimer, F. Ace. Chem. Res. 1972, 5, 81-91.
24. de Graaff, R. A. G.; Gorter, S.; Romers, C.; Wong, H. N. C.; Sondheimer, F. J. Chem. Soc., Perkin Trans. 2 1981, 478-480.
25. Baldwin, K. P.; Matzger, A. J.; Scheiman, D. A.; Tessier, C. A.; Vollhardt, K. P. C.; Youngs, W. J. Synlett 1995, 1215-1218.
26. Zhou, Q.; Carroll, P. J.; Swager, T. M. J. Org. Chem. 1994, 59, 1294-1301.
27. Boese, R.; Matzger, A. J.; Vollhardt, K. P. C. J. Am. Chem. Soc. 1997, 119, 2052-2053.
28. Dosa, P. L; Erben, C.; lyer, V. S.; Vollhardt, K. P. C.; Wasser, I. M. J. Am. Chem. Soc. 1999, 121, 10430-10431.
29. Kiang, C.-H.; Goddard.W. A., III Phys. Rev. Lett. 1996, 76, 25152518.
30. Rubin, Y.; Parker, T. C.; Pastor, S. J.; Jalisatgi, S.; Boulle, C.; Wilkins, C. L. Angew. Chem., Int. Ed. 1998, 37, 1226-1229.
31. Tobe, Y.; Fujii, T.; Matsumoto, H.; Tsumuraya, K.; Noguchi, D.; Nakagawa, N.; Sonoda, M.; Naemura, K.; Achiba, Y.; Wakabayashi, T. J. Am. Chem. Soc. 2000, 722, 1762-1775.
32. Tobe, Y.; Nakanishi, H.; Sonoda, M.; Wakabayashi, T.; Achiba, Y. Chem. Commun. 1999, 1625-1626.
33. Tobe, Y.; Nakagawa, N.; Naemura, K.; Wakabayashi, T.; Shida, T.; Achiba, Y. J. Am. Chem. Soc. 1998, 120, 4544-4545.
34. Bunz, U. H. F.; Roidl, G.; Altmann, M.; Enkelmann, V.; Shimizu, K. D. J. Am. Chem. Soc. 1999, 121, 10719-10726.
35. Tykwinski, R. R.; Diederich, F.; Grämlich, F.; Seiler, P. Helv. Chim. Acta 1996, 79, 634-645.
36. Fallis, A. G. Can. J. Chem. 1999, 77, 159-177.
37. Goroff, N. S. Acc. Chem. Res. 1996, 29, 77-83.
38. Meier, H. Adv. Strain Org. Chem. 1991, l, 215-272.
39. Misumi, S.; Kaneda, T. In The Chemistry of the Carbon-Carbon Triple Bond Part 2; Patai, S., Ed.; John Wiley & Sons: Chichester, 1978; pp 713-737.
40. (a) Gleiter, R.; Merger, R.; Chavez, J.; Oeser, T.; Irngartinger, H.; Pritzkow, H.; Nuber, B. Fur. J. Org. Chem. 1999, 2841-2843.
41. (b) Haberhauer, G.; Gleiter, R.; Irngartinger, H.; Oeser, T.; Rominger, F. J. Chem. Soc., Perkin Trans. 2 1999, 2093-2097.
42. Gleiter, R.; Haberhauer, G.; Irngartinger, H.; Oeser, T.; Rominger, F. OrganometaUics 1999, 18, 3615-3622.
43. Stahr, H.; Gleiter, R.; Haberhauer, G.; Irngartinger, H.; Oeser, A. Chem. Ber. 1997, 130, 1807-1811.
44. (e) Gleiter, R.; Merger, R. In Modem Acetylene Chemistry; Stang, P. J., Diederich, F., Eds.; VCH: Weinheim, 1995; pp 285-319.
45. (0 Gleiter, R.; Schäfer, W.; Flatow, A. J. Org. Chem. 1984, 49, 372-374.
46. (a) Scott, L. T.; Cooney, M. J. In Modem Acetylene Chemistry; Stang, P. J., Diederich, F., Eds.; VCH: Weinheim, 1995; pp 321-351.
47. (b) Scott, L. T.; Cooney, M. J.; Otte, C.; Puls, C.; Haumann, T.; Boese, R.; Carroll, R. J.; Smith, A. B., III; de Meijere, A. J. Am. Chem. Soc. 1994, 116, 10275-10283.
48. Matsuoka, T.; Negi, T.; Otsubo, T.; Sakata, Y.; Misumi, S. Bull. Chem. Soc. Jpn. 1972, 45, 1825-1833.
49. (a) Toda, F.; Ando, T.; Kataoka, M.; Nakagawa, M. Bull. Chem. Soc. Jpn. 1971, 44, 1914-1916.
50. (b) Kataoka, M.; Ando, T.; Nakagawa, M. Bull. Chem. Soc. Jpn. 1971, 44, 1909-1914.
51. Kataoka, M.; Ando, T.; Nakagawa, M. Bull. Chem. Soc. Jpn. 1971, 44, 177-184.
52. Ando, T.; Nakagawa, M. Bull. Chem. Soc. Jpn. 1971, 44, 172-177.
53. (e) Toda, F.; Nakagawa, M. Bull. Chem. Soc. Jpn. 1961, 34, 874-786.
54. (0 Toda, F.; Nakagawa, M. Bull. Chem. Soc. Jpn. 1961, 34, 862-874.
55. (g) Toda, F.; Nakagawa, M. Bull. Chem. Soc. Jpn. 1960, 33, 223-230.
56. Eisler, S.; Tykwinski, R. R. Ange\v. Chem., Int. Ed. 1999, 38, 19401943.
57. Other examples of expanded radialenes: (a) Schreiber, M.; Tykwinski, R. R.; Diederich, F.; Spreiter, R.; Gubler, U.; Bosshard, C; Poberaj, I.; Günter, P.; Boudon, C.; Gisselbrecht, J.-P.; Gross, M.; Jonas, U.; Ringsdorf, H. Adv. Mater. 1997, 9, 339-343.
58. (b) Anthony, J.; Boldi, A. M.; Boudon, C.; Gisselbrecht, J.-P.; Gross, M.; Seiler, P.; Knobler, C. B.; Diederich, F. Helv. Chim. Acta 1995, 78, 797-817.
59. Boldi, A. M.; Diederich, F. Angew. Chem., Int. Ed. Engt. 1994, 33, 468-471.
60. Baughman, R. H.; Yee, K. C. J. Polym. Sci. Macromol. Rev. 1978, 13, 219-239.
61. Polydiacetylenes; Bloor, D., Chance, R. R., Eds.; Martinus Nijhoff: Dordrecht, 1985.
62. Wegner, G. Makromol. Chem., Snppl. 1984, 6, 347-357.
63. Wegner, G. Makromol. Chem. 1972, 154, 35-48.
64. For a preliminary communication of 8c-e, see: Tykwinski, R. R. Chem. Commun. 1999, 905-906.
65. Hopf, H. Angew. Chem., Int. Ed. Engl. 1984, 23, 948-960.
66. Stang, P. J.; Fisk, T. E. Synthesis 1979, 438-440.
67. Zhao, Y.; Tykwinski, R. R. J. Am. Chem. Soc. 1999, 121, 458459.
68. Hay, A. S. J. Org. Chem. 1962, 27, 3320-3321.
69. Powder samples of 8d show darkening at ca. 115 °C, and a reproducible melting point at ca. 155 °C. Continued heating gives rapid decomposition to a black solid at 165 °C. Differential scanning calorimetery of microcrystalline 8d showed a distinct melting point at 160 °C, followed almost immediately by decomposition or polymerization. These observations suggested a topochemical reaction/polymerization involving the diacetylene moiety to a polydiacetylene (PDA) product. Analysis of the crystal packing of 8d, however, shows the closest distance between atoms of the diacetylene groups to be greater than 7 A, rendering PDA formation via a 1, 4-addition pattern unlikely (see: Enkelmann, V. Adv. Polym. Sci. 1984, 63, 91-136). Analysis of the orange-colored material from the above experiments by 'H NMR and MS shows predominantly the macrocycle 8d. To date, the source of the discoloration remains unresolved, and investigations of the thermochemistry of 8d are currently ongoing.
70. The numbering scheme shown for structure 8c in Figure 1 has been changed from that used in ref 43 to facilitate comparisons to the other structures.
71. AMI forcefield, MacSpartan Plus 1.1.9, Wavefunction, Inc., 1998.
72. 13C NMR shifts of C(4)/C(12) for 8c-e were incorrectly reported in ref 43.
73. Kalinowski, H. O.; Berger, S.; Braun, S. Carbon-13 NMR Spectroscopy; John Wiley & Sons: Chichester, 1988.
74. Neidlein, R.; Winter, M. Synthesis 1998, 1362-1366.
75. Wong, H. N. C.; Sondheimer, F. Tetrahedron 1981, 37, W99W109.
76. 13C NMR chemical shift data with bond angle a about acetylenic carbons C(2)/C(17), C(3)/ C(16), C(8)/C(11), and C(9)/C(IO).
77. Gleiter, R.; Kratz, D.; Schäfer, W.; Schehlmann, V. J. Am. Chem. Soc. 1991, 113, 9258-9264.
78. Gleiter, R.; Merger, R.; Irngartinger, H. J. Am. Chem. Soc. 1992, 114, 8927-8932.
79. Hopf, H.; Maas, G. Angnv. Cltem., Int. Ed. Engl. 1992, 31, 931-954.
80. Armitage, J. B.; Whiting, M. C. J. Chem. Soc. 1952, 2005-2010.
81. Badger, R. M. J. Chem. Phys. 1934, 2, 128-131.
82. Gordy, W. J. Chem. Phys. 1946, 14, 305-320.
83. 1H NMR analysis.
84. 13C NMR chemical shift data for carbons C(4)/C(12) and C(5)/C(13), and b) olefinic Raman frequencies with bond angle a C(3)-C(4)-C(8)/C(11)-C(12)-C(16).
85. See Supporting Information for correlations of acetylenic Raman frequencies with bond angle a about carbons C(8)/C(11) and C(9)/C(10).
86. Bellamy, L. J. Advances in Infrared Group Frequencies; Methuen: London, 1968.
87. Detert, H.; Meier, H. Liebigs Ann./Recl. 1997, 1565-1570.
88. Brandsma, L. Preparative Acetylenic Chemistry, 2nd ed.; Eisevier: Amsterdam, 1988.