Pure and Applied Chemistry, 2008, Volume 80, No. 3, pp. 533-546, References

Pure Appl. Chem., 2008, Vol. 80, No. 3, pp. 533-546

http://dx.doi.org/10.1351/pac200880030533

Nonplanar aromatic compounds. Part 10: A strategy for the synthesis of aromatic belts-all wrapped up or down the tubes?

Tieguang Yao, Hao Yu, Rudolf J. Vermeij and Graham J. Bodwell

Department of Chemistry, Memorial University, St. John's, NL A1B 3X7, Canada

References

1. A. Schroder, H.-B. Mekelburger, F. Vogtle. Top. Curr. Chem. 172, 179 (1994).
2. R. Herges. In Modern Cyclophane Chemistry, R.Gleiter, H. Hopf (Eds.), Chap. 13, pp. 337-358, Wiley-VCH, Weinheim (2004).
3. (a). Z. Chen, D. Jiang, X. Lu, H. Bettinger, S. Dai, P. v. R. Schleyer, K. N. Houk. Org. Lett. 9, 5449 (2007);
3. (b). K. Tahara, Y. Tobe. Chem. Rev. 107, 5274 (2007);
3. (c). L. Turker, S. Gumus. J. Mol. Struct. (Theochem) 685, 1 (2004); (http://dx.doi.org/10.1016/j.theochem.2004.04.021)
3. (d). K. N. Houk, P. S. Lee, M.Nendel. J. Org. Chem. 66, 5517 (2001); (http://dx.doi.org/10.1021/jo010391f)
3. (e). M. Guillaume, B. Champagne, E. A. Perpete, J.M.Andre. Theor. Chem. Acc. 105, 431 (2001); (http://dx.doi.org/10.1007/s002140000245)
3. (f). K. Tahara, Y. Tobe. Chem. Rev. 107, 5274 (2007).
4. (a). A. A. Fokin, H. Jiao, P. v. R. Schleyer. J. Am. Chem. Soc. 120, 9364 (1998); (http://dx.doi.org/10.1021/ja9810437)
4. (b). A. B. McEwen, P. v. R. Schleyer. J. Org. Chem. 51, 4357 (1986). (http://dx.doi.org/10.1021/jo00373a006)
5. (a). U. Giresser, D. Giuffrida, F. H. Kohnke, J. P. Mathias, D. Philip, J. F. Stoddart. Pure Appl. Chem. 65, 119 (1993); (http://dx.doi.org/10.1351/pac199365010119)
5. (b). P. R. Ashton, G. R. Brown, N. S. Isaacs, D. Giuffrida, F. H. Kohnke, J. P. Mathias, A. M. Z. Slawin, D. R. Smith, J. F. Stoddart, D. J. Williams. J. Am. Chem. Soc. 114, 6330 (1992); (http://dx.doi.org/10.1021/ja00042a009)
5. (c). F. H. Kohnke, J. F. Stoddart. Pure Appl. Chem. 61, 1581 (1989). (http://dx.doi.org/10.1351/pac198961091581)
6. (a). R. M. Cory, C. L. McPhail. Adv. Theor. Interesting Mol. 4, 53 (1998);
6. (b). R. M. Cory, C. L. McPhail. Tetrahedron Lett. 37, 1987 (1996); (http://dx.doi.org/10.1016/0040-4039(96)00264-X)
6. (c). R. M. Cory, C. L. McPhail, A. J. Dikmans, J. J. Vittal. Tetrahedron Lett. 37, 1983 (1996). (http://dx.doi.org/10.1016/0040-4039(96)00263-8)
7. J. Benkhoff, R. Boese, F.-G. Klarner, A. E. Wigger. Tetrahedron Lett. 35, 73 (1994). (http://dx.doi.org/10.1016/0040-4039(94)88165-0)
8. (a). B. Esser, J. A. Raskatov, R. Gleiter. Org. Lett. 9, 4037 (2007); (http://dx.doi.org/10.1021/ol701763b)
8. (b). R. Gleiter, B. Hellbach, S.Gath, R. J. Schaller. Pure Appl. Chem. 78, 699 (2006); (http://dx.doi.org/10.1351/pac200678040699)
8. (c). B. Hellbach, F. Rominger, R. Gleiter. Angew. Chem., Int. Ed. 43, 5846 (2004). (http://dx.doi.org/10.1002/anie.200460772)
9. (a). C. Denekamp, A. Etinger, W. Amrein, A. Stanger, M. Stuparu, A.-D. Schluter. Chem.Eur. J. 14, 1628 (2008); (http://dx.doi.org/10.1002/chem.200701098)
9. (b). M. Stuparu, V. Gramlich, A. Stanger, A. D. Schluter. J. Org. Chem. 72, 424 (2007); (http://dx.doi.org/10.1021/jo0617114)
9. (c). M.Stuparu, D. Lentz, H. Ruegger, A. D. Schluter. Eur. J. Org. Chem. 88 (2007); (http://dx.doi.org/10.1002/ejoc.200600698)
9. (d). W. D. Neudorff, D. Lentz, M. Anibarro, A. D. Schluter. Chem.Eur. J. 9, 2745 (2003). (http://dx.doi.org/10.1002/chem.200304824)
10. A. Godt, V. Enkelmann, A.-D. Schluter. Angew. Chem., Int. Ed. Engl. 28, 1680 (1989). (http://dx.doi.org/10.1002/anie.198916801)
11. O. Kintzel, P. Luger, M. Weber, A.-D. Schluter. Eur. J. Org. Chem. 99 (1998). (http://dx.doi.org/10.1002/(SICI)1099-0690(199801)1998:1<99::AID-EJOC99>3.0.CO;2-C)
12. G. P. Miller, S. Okano, D. Tomanek. J. Chem. Phys. 124, Art. No. 121102 (2006). (http://dx.doi.org/10.1063/1.2187968)
13. (a). J. Aihara. J. Chem. Soc., Perkin Trans. 2 971 (1994); (http://dx.doi.org/10.1039/p29940000971)
13. (b). Y. Matsuo, K. Tahara, E.Nakamura. Org. Lett. 5, 3181 (2003). (http://dx.doi.org/10.1021/ol0349514)
14. (a). Y. Matsuo, K. Tahara, K. Morita, K. Matsuo, E. Nakamura. Angew. Chem., Int. Ed. 46, 2844 (2007); (http://dx.doi.org/10.1002/anie.200604839)
14. (b). Y. Matsuo, K. Tahara, M. Sawamura, E. Nakamura. J. Am. Chem. Soc. 126, 8725 (2004); (http://dx.doi.org/10.1021/ja048683w)
14. (c). E. Nakamura, K. Tahara, Y. Matsuo, M. Sawamura. J. Am. Chem. Soc. 125, 2834 (2003). (http://dx.doi.org/10.1021/ja029915z)
15. (a). Y. Kuwatani, T. Yoshida, A. Kusaka, M. Oda, K. Hara, M. Yoshida, H. Matsuyama, M. Iyoda. Tetrahedron 57, 3567 (2001); (http://dx.doi.org/10.1016/S0040-4020(01)00244-7)
15. (b). Y. Kuwatani, T. Yoshida, A. Kusaka, M. Iyoda. Tetrahedron Lett. 41, 359 (2000). (http://dx.doi.org/10.1016/S0040-4039(99)02062-6)
16. (a). M. A. Brooks. Ph.D. dissertation, Boston College, Chestnut Hill, MA (1998);
16. (b). St. H. M. Martin-Davis. Ph.D. dissertation, Boston College, Chestnut Hill, MA (2002).
17. F. Vogtle. Top. Curr. Chem. 115, 157 (1983).
18. R. H. Mitchell. Heterocycles 11, 563 (1978).
19. (a). W. Boomgaarden, F. Vogtle, M. Nieger, H. Hupfer. Chem.Eur. J. 5, 345 (1999); (http://dx.doi.org/10.1002/(SICI)1521-3765(19990104)5:1<345::AID-CHEM345>3.0.CO;2-T)
19. (b). S.Breidenbach, J. Harren, S. Neumann, M. Nieger, K. Rissanen F. Vogtle. J. Chem. Soc., Perkin Trans. 1 2061 (1996);
19. (c). S. Breidenbach, S. Ohren, F. Vogtle. Chem.Eur. J. 2, 832 (1996); (http://dx.doi.org/10.1002/chem.19960020716)
19. (d). S. Breidenbach, S. Ohren, R. Herbst-Irmer, S. Kotila, M. Nieger, F. Vogtle. Liebigs Ann. 2115 (1996);
19. (e). S. Breidenbach, S. Ohren, M. Nieger, F. Vogtle. J. Chem. Soc., Chem. Commun. 1237 (1995); (http://dx.doi.org/10.1039/c39950001237)
19. (f). W. Josten, S. Neumann, F. Vogtle, K. Hagele, M. Przybylski, F. Beer, K. Mullen. Chem. Ber. 127, 2089 (1994); (http://dx.doi.org/10.1002/cber.19941271035)
19. (g). W. Josten, D. Karbach, M. Nieger, F. Vogtle, K. Hagele, M.Svoboda, M. Przybylski. Chem. Ber. 127, 767 (1994); (http://dx.doi.org/10.1002/cber.19941270428)
19. (h). A. Schroder, D. Karbach, F. Vogtle. Chem. Ber. 125, 1881 (1992); (http://dx.doi.org/10.1002/cber.19921250815)
19. (i). F. Vogtle, A. Schroder, D. Karbach. Angew. Chem., Int. Ed. Engl. 30, 575 (1991). (http://dx.doi.org/10.1002/anie.199105751)
20. L. T. Scott. Angew. Chem., Int. Ed. 42, 4133 (2003). (http://dx.doi.org/10.1002/anie.200301671)
21. (a). T. Kawase. J. Synth. Org. Chem. Japan 65, 888 (2007);
21. (b). T. Kawase, H. Kurata. Chem. Rev. 106, 5250 (2006); (http://dx.doi.org/10.1021/cr0509657)
21. (c). T. Kawase, M. Oda. Pure Appl. Chem. 78, 831 (2006). (http://dx.doi.org/10.1351/pac200678040831)
22. R. H. Mitchell, V. Boekelheide. J. Am. Chem. Soc. 92, 3510 (1970). (http://dx.doi.org/10.1021/ja00714a071)
23. I. Fleming. Frontier Orbitals and Organic Chemical Reactions, John Wiley, New York (1982).
24. G. J. Bodwell, J. N. Bridson, S.-L. Chen, R. A. Poirier. J. Am. Chem. Soc. 123, 4704 (2001). (http://dx.doi.org/10.1021/ja002901d)
25. (a). G. J. Bodwell, J. N. Bridson, T. J. Houghton, J. W. J. Kennedy, M. R. Mannion. Angew. Chem. 108, 1418 (1996); (http://dx.doi.org/10.1002/ange.19961081211)
25. (b). G. J. Bodwell, J. N. Bridson, T. J. Houghton, J. W. J. Kennedy, M. R. Mannion. Angew. Chem., Int. Ed. Engl. 35, 1320 (1996); (http://dx.doi.org/10.1002/anie.199613201)
25. (c). G. J. Bodwell, J. N. Bridson, T. J. Houghton, J. W. J. Kennedy, M. R. Mannion. Chem.Eur. J. 5, 1823 (1999); (http://dx.doi.org/10.1002/(SICI)1521-3765(19990604)5:6<1823::AID-CHEM1823>3.0.CO;2-I)
25. (d). G. J. Bodwell, J.N. Bridson, M. Cyranski, J. W. J. Kennedy, T. M. Krygowski, M. R. Mannion, D. O. Miller. J. Org. Chem. 68, 2089 (2003). (http://dx.doi.org/10.1021/jo0206059)
26. G. J. Bodwell, T. J. Houghton, H. E. Koury, B. Yarlagadda. Synlett 751 (1995). (http://dx.doi.org/10.1055/s-1995-5065)
27. R. F. Borch. J. Org. Chem. 34, 627 (1969). (http://dx.doi.org/10.1021/jo01255a031)
28. (a). G. J. Bodwell, J. J. Fleming, M. R. Mannion, D. O. Miller. J. Org. Chem. 65, 5360 (2000); (http://dx.doi.org/10.1021/jo0007027)
28. (b). I. Aprahamian, G. J. Bodwell, J. J. Fleming, G. P. Manning, M. R. Mannion, B. L. Merner, T.Sheradsky, R. J. Vermeij, M. Rabinovitz. J. Am. Chem. Soc. 126, 6765 (2004); (http://dx.doi.org/10.1021/ja040039u)
28. (c). G. J. Bodwell, D. O. Miller, R. J. Vermeij. Org. Lett. 3, 2093 (2001). (http://dx.doi.org/10.1021/ol016053i)
29. G. J. Bodwell, J. J. Fleming, D. O. Miller. Tetrahedron 57, 3577 (2001). (http://dx.doi.org/10.1016/S0040-4020(01)00245-9)
30. M. B. Smith, J. March. March's Advanced Organic Chemistry, 5th ed., p. 20, John Wiley, New York (2001).
31. (b) M. K. Cyranski M. A. Dobrowolski, B. L. Merner, G. J. Bodwell, J. Wu, P. v. R. Schleyer. Manuscript under review.
32. (a). T. Umemoto, T. Kawashima, Y. Sakata, S. Misumi. Tetrahedron Lett. 1005 (1975); (http://dx.doi.org/10.1016/S0040-4039(00)72628-1)
32. (b). T.Umemoto, T. Otsubo, Y. Sakata, S. Misumi. Tetrahedron Lett. 593 (1973). (http://dx.doi.org/10.1016/S0040-4039(01)95854-X)
33. (a). T. Otsubo, V. Boekelheide. Tetrahedron Lett. 3881 (1975); (http://dx.doi.org/10.1016/S0040-4039(00)91244-9)
33. (b). T. Otsubo, V. Boekelheide. J. Org. Chem. 42, 1085 (1977). (http://dx.doi.org/10.1021/jo00426a036)
34. (a). G. J. Bodwell, K. M. Hawco, T. Satou. Synlett 879 (2003); (http://dx.doi.org/10.1055/s-2003-38746)
34. (b). G. J. Bodwell, K. M. Hawco, R. P. da Silva. Synlett 179 (2003). (http://dx.doi.org/10.1055/s-2003-36800)
34. (i). bromination with Br2,
36. (ii) oxidation with KMnO4 and
37. (iii) esterification with EtOH, H2SO4.
37. (a). L. C. Campeau, D. R. Stuart, K. Fagnou. Aldrichim. Acta 40, 35 (2007);
37. (b). L. C. Campeau, M. Parisien, M. Leblanc, K. Fagnou. J. Am. Chem. Soc. 126, 9186 (2004). (http://dx.doi.org/10.1021/ja049017y)

Pure and Applied Chemistry

Navigation

PAC Archives

RSS Feeds

Highlights

Nonplanar aromatic compounds. Part 10: A strategy for the synthesis of aromatic belts-all wrapped up or down the tubes?

References

Pure and Applied Chemistry

Navigation

Search PAC

PAC Archives

RSS Feeds

Highlights

Nonplanar aromatic compounds. Part 10: A strategy for the synthesis of aromatic belts-all wrapped up or down the tubes?

References