Synthesis and relative diatropicity of a remarkably aromatic thia[13]annulene

Journal of the American Chemical Society

Volumn 118, Issue 4, 1996, Pages 722-725

  Mitchell, Reginald H ^a   Iyer, Vivekanantan S ^a  

^a UNIVERSITY OF VICTORIA   (Canada)

Author keywords

[No Author keywords available]

Indexed keywords

EID: 0001556759     PISSN: 00027863     EISSN: None     Source Type: Journal    
DOI: 10.1021/ja953025k     Document Type: Article

References (33)

1. For a recent review see: Minkin, V. J.; Glukhovtsev, M. N.; Simkin, B. Y. Aromaticity and Anttaromaticity: Electronic and Structural Aspects. Wiley. New York; 1994.
2. von Ragué Schleyer, P.; Freeman, P. K.; Jiao, H.; Goldfuss, B. Angew. Chem., Int. Ed. Engl. 1995, 34, 337-340. This paper also quotes many of the previous references on the topic.
3. Balaban, A. T ; Banciu, M.; Ciorba, V. Annulenes. Benzo-, Hetero-, Homo-Derivatives: CRC Press: Boca Raton, FL, 1987; Vol. I, pp 207-214 and Vol. III, pp 19-27.
4. Balaban, A. T ; Banciu, M.; Ciorba, V. Annulenes. Benzo-, Hetero-, Homo-Derivatives: CRC Press: Boca Raton, FL, 1987; Vol. I, pp 207-214 and Vol. III, pp 19-27.
5. Beeby, P. J., Weavers, R. T.; Sondheimer, F. Angew. Chem., Int. Ed. Engl. 1974, 13, 138-139.
6. Schroder, G., Plinke, G.; Oth, J. F. M. Angew. Chem., Int. Ed. Engl. 1972, 11, 424-426. Schroder, G.; Heil, G.; Rottele, H ; Oth, J. F. M. Angew. Chem., Int. Ed. Engl. 1972, 11, 426-427.
7. Schroder, G., Plinke, G.; Oth, J. F. M. Angew. Chem., Int. Ed. Engl. 1972, 11, 424-426. Schroder, G.; Heil, G.; Rottele, H ; Oth, J. F. M. Angew. Chem., Int. Ed. Engl. 1972, 11, 426-427.
8. Okazaki, R.; Hasegawa, T., Shishido, Y. J. Am. Chem. Soc. 1984, 106, 5271-5273.
9. Kato, H., Toda, S., Arikawa, Y.; Masuzawa, M.; Hashimoto, M.; Ikomoa, K.; Wang, S Z., Miyasaka, A. J. Chem. Soc. Perkin Trans. 1, 1990, 2035-2040
10. Wife, R. L., Sondheimer, F. J. Am. Chem. Soc. 1975, 97, 640-641.
11. Ojima, J.; Nagaya, M.; Katsuyama, J.; Yamamoto, G. J. Chem. Soc. Perkin Trans. 1, 1990, 869-879.
12. Ojima, J.; Hashimoto, T.; Katsuyama, J.; Miyashita, H.; Fujita, S.; Kuroda, S.; Kano, Y.; Yamamoto, G. J. Chem. Soc., Perkin Trans. 1, 1990, 333-343
13. Mitchell, R. H.; Iyer, V. S.; Khalifa, N.; Mahadevan, R.; Venugopalan, S.; Weerawarna, S. A.; Zhou, P. J. Am. Chem. Soc. 1995, 117, 1514-1532.
14. Mitchell, R. H. Adv. Theor. Interesting Mol. 1989, 1, 135-199.
15. Mitchell, R. H.; Boekelheide, V. J. Am. Chem. Soc. 1974, 96, 1547-1557.
16. Performed using HyperChem. Version 2.
17. Gewald, K.; Schinke, E.; Bottcher, H. Chem. Ber. 1966, 99, 94-100. See also: Sampson, N. S.; Bartlett, P. A. J. Org. Chem. 1991, 56, 7179-7183
18. Gewald, K.; Schinke, E.; Bottcher, H. Chem. Ber. 1966, 99, 94-100. See also: Sampson, N. S.; Bartlett, P. A. J. Org. Chem. 1991, 56, 7179-7183
19. Kellog, R. M.; Schaap, A. P., Harper, E. T.: Wynberg, H. J. Org. Chem. 1968, 33, 2902-2909.
20. The reverse coupling, using the bis-thiol of 12 and the bis-bromide of 13, gave only 55% yield of the same anti/syn ratio. The thiol was not very stable.
21. Mitchell, R. H.; Otsubo, T., Boekelheide, V. Tetrahedron Lett. 1975. 16, 219-222.
22. Calculated using PCMODEL 386, V4.0 from Serena Software, Box 3076, Bloomington, IN 47402-3076. This is an MM2+Pi calculation, and in our experience gives good values for geometries of annulenes and cyclophanes.
23. See for example: Garratt, P. J. In Aromaticity, Wiley-Interscience: New York, 1986; p 292. Aihara, J Pure Appl. Chem. 1982, 54, 1115-1128. Zhou, Z. Int. Rev. Phys. Chem. 1992, 11, 243-261.
24. See for example: Garratt, P. J. In Aromaticity, Wiley-Interscience: New York, 1986; p 292. Aihara, J Pure Appl. Chem. 1982, 54, 1115-1128. Zhou, Z. Int. Rev. Phys. Chem. 1992, 11, 243-261.
25. See for example: Garratt, P. J. In Aromaticity, Wiley-Interscience: New York, 1986; p 292. Aihara, J Pure Appl. Chem. 1982, 54, 1115-1128. Zhou, Z. Int. Rev. Phys. Chem. 1992, 11, 243-261.
26. Haddon, R. C. Tetrahedron 1972, 28, 3635-3655.
27. Mitchell, R. H.; Zhou, P. Tetrahedron Lett. 1991, 32, 6319-6322. While 18 could be considered as a [14]annulene fused to a furan, rather than an oxa[17]annulene, the contribution to the ring current from the [14]-annulene will be rather small because of the disfavored structure with a delocalized bond fused to both the [14]annulene and furan structures.
28. Boekelheide, V., Pepperidine, W. J. Am. Chem. Soc. 1970, 92, 3684-3688.
29. Cremer, D.; Gunther, H. Justus Liebigs Ann. Chem. 1972, 763, 87-108.
30. Steinkopf, W.; Jacob, H. Justus Liebigs Ann. Chem. 1935, 515, 273.
31. Okamoto, T.; Kakinami, T.; Fujimoto, H.; Kajigaeshi. S. Bull. Chem. Soc. Jpn. 1991, 64, 2566-2568.
32. Dapperheld, S.; Feldhues, M.; Litterer, H.; Sistig, F.; Wegener, P. Synthesis 1990, 403-405.
33. Borch, R. F. J. Org. Chem. 1969, 34, 627-629.