2,5,8,11,14,17-Hexa-t-butyldecacyclene and 1,7,13-/1,6,12-tri-t-butyldecacyclene: Possible precursors for bowl-shaped polycyclic arenes

Tetrahedron Letters

Volumn 37, Issue 46, 1996, Pages 8371-8374

  Zimmermann, Klaus ^a   Goddard, Richard ^a   Krüger, Carl ^a   Haenel, Matthias W ^a  

^a MAX PLANCK INSTITUT FÜR KOHLENFORSCHUNG   (Germany)

Author keywords

[No Author keywords available]

Indexed keywords

POLYCYCLIC AROMATIC HYDROCARBON;

ARTICLE; DRUG SYNTHESIS; REACTION ANALYSIS;

EID: 0030580303     PISSN: 00404039     EISSN: None     Source Type: Journal    
DOI: 10.1016/0040-4039(96)01933-8     Document Type: Article

References (31)

1. 1) The present work is part of the doctoral thesis of K. Zimmermann, University of Düsseldorf, 1996.
2. 2) Barth, W.E.; Lawton, R.G. J. Am. Chem. Soc. 1966, 88, 380-381; Barth, W.E.; Lawton, R.G. J. Am. Chem. Soc. 1971, 93, 1730-1745; Hanson, J.C.; Nordman, C.E. Acta Cryst. Sect. B. 1976, 32, 1147-1153; Scott, L.T.; Hashemi, M.M.; Meyer, D.T.; Warren, H.B. J. Am. Chem. Soc. 1991, 113, 7082-7084; Scott, L.T.; Hashemi, M.M.; Bratcher, M.S. J. Am. Chem. Soc. 1992, 114, 1920-1921; Borchert, A.; Fuchicello, A.; Kilway, K.V.; Baldridge, K.K.; Siegel, J.S. J. Am. Chem. Soc. 1992, 114, 1921-1923.
3. 2) Barth, W.E.; Lawton, R.G. J. Am. Chem. Soc. 1966, 88, 380-381; Barth, W.E.; Lawton, R.G. J. Am. Chem. Soc. 1971, 93, 1730-1745; Hanson, J.C.; Nordman, C.E. Acta Cryst. Sect. B. 1976, 32, 1147-1153; Scott, L.T.; Hashemi, M.M.; Meyer, D.T.; Warren, H.B. J. Am. Chem. Soc. 1991, 113, 7082-7084; Scott, L.T.; Hashemi, M.M.; Bratcher, M.S. J. Am. Chem. Soc. 1992, 114, 1920-1921; Borchert, A.; Fuchicello, A.; Kilway, K.V.; Baldridge, K.K.; Siegel, J.S. J. Am. Chem. Soc. 1992, 114, 1921-1923.
4. 2) Barth, W.E.; Lawton, R.G. J. Am. Chem. Soc. 1966, 88, 380-381; Barth, W.E.; Lawton, R.G. J. Am. Chem. Soc. 1971, 93, 1730-1745; Hanson, J.C.; Nordman, C.E. Acta Cryst. Sect. B. 1976, 32, 1147-1153; Scott, L.T.; Hashemi, M.M.; Meyer, D.T.; Warren, H.B. J. Am. Chem. Soc. 1991, 113, 7082-7084; Scott, L.T.; Hashemi, M.M.; Bratcher, M.S. J. Am. Chem. Soc. 1992, 114, 1920-1921; Borchert, A.; Fuchicello, A.; Kilway, K.V.; Baldridge, K.K.; Siegel, J.S. J. Am. Chem. Soc. 1992, 114, 1921-1923.
5. 2) Barth, W.E.; Lawton, R.G. J. Am. Chem. Soc. 1966, 88, 380-381; Barth, W.E.; Lawton, R.G. J. Am. Chem. Soc. 1971, 93, 1730-1745; Hanson, J.C.; Nordman, C.E. Acta Cryst. Sect. B. 1976, 32, 1147-1153; Scott, L.T.; Hashemi, M.M.; Meyer, D.T.; Warren, H.B. J. Am. Chem. Soc. 1991, 113, 7082-7084; Scott, L.T.; Hashemi, M.M.; Bratcher, M.S. J. Am. Chem. Soc. 1992, 114, 1920-1921; Borchert, A.; Fuchicello, A.; Kilway, K.V.; Baldridge, K.K.; Siegel, J.S. J. Am. Chem. Soc. 1992, 114, 1921-1923.
6. 2) Barth, W.E.; Lawton, R.G. J. Am. Chem. Soc. 1966, 88, 380-381; Barth, W.E.; Lawton, R.G. J. Am. Chem. Soc. 1971, 93, 1730-1745; Hanson, J.C.; Nordman, C.E. Acta Cryst. Sect. B. 1976, 32, 1147-1153; Scott, L.T.; Hashemi, M.M.; Meyer, D.T.; Warren, H.B. J. Am. Chem. Soc. 1991, 113, 7082-7084; Scott, L.T.; Hashemi, M.M.; Bratcher, M.S. J. Am. Chem. Soc. 1992, 114, 1920-1921; Borchert, A.; Fuchicello, A.; Kilway, K.V.; Baldridge, K.K.; Siegel, J.S. J. Am. Chem. Soc. 1992, 114, 1921-1923.
7. 2) Barth, W.E.; Lawton, R.G. J. Am. Chem. Soc. 1966, 88, 380-381; Barth, W.E.; Lawton, R.G. J. Am. Chem. Soc. 1971, 93, 1730-1745; Hanson, J.C.; Nordman, C.E. Acta Cryst. Sect. B. 1976, 32, 1147-1153; Scott, L.T.; Hashemi, M.M.; Meyer, D.T.; Warren, H.B. J. Am. Chem. Soc. 1991, 113, 7082-7084; Scott, L.T.; Hashemi, M.M.; Bratcher, M.S. J. Am. Chem. Soc. 1992, 114, 1920-1921; Borchert, A.; Fuchicello, A.; Kilway, K.V.; Baldridge, K.K.; Siegel, J.S. J. Am. Chem. Soc. 1992, 114, 1921-1923.
8. 3) Rabideau, P.W.; Abdourazak, A.H.; Folsom, H.E.; Marcinow, Z.; Sygula, A.; Sygula, R. J. Am. Chem. Soc. 1994, 116, 7891-7892; Abdourazak, A.H.; Marcinow, Z.; Sygula, A.; Sygula, R.; Rabideau, P.W. J. Am. Chem. Soc. 1995, 117, 6410-6411; Rabideau, P.W.; Sygula, A. Acc. Chem. Res. 1996, 29, 235-242, and references therein.
9. 3) Rabideau, P.W.; Abdourazak, A.H.; Folsom, H.E.; Marcinow, Z.; Sygula, A.; Sygula, R. J. Am. Chem. Soc. 1994, 116, 7891-7892; Abdourazak, A.H.; Marcinow, Z.; Sygula, A.; Sygula, R.; Rabideau, P.W. J. Am. Chem. Soc. 1995, 117, 6410-6411; Rabideau, P.W.; Sygula, A. Acc. Chem. Res. 1996, 29, 235-242, and references therein.
10. 3) Rabideau, P.W.; Abdourazak, A.H.; Folsom, H.E.; Marcinow, Z.; Sygula, A.; Sygula, R. J. Am. Chem. Soc. 1994, 116, 7891-7892; Abdourazak, A.H.; Marcinow, Z.; Sygula, A.; Sygula, R.; Rabideau, P.W. J. Am. Chem. Soc. 1995, 117, 6410-6411; Rabideau, P.W.; Sygula, A. Acc. Chem. Res. 1996, 29, 235-242, and references therein.
11. 4) A systematic name for the target molecule 3 is benz[1″,2″,3″:3′,4′;6″:9]-as-indaceno-[1′,2′,3′,8′:1,2,3,10;8′,7′,6′,5′-atuv]acephenanthro[6,5,4,3-opqrs]picene.
12. 60 were formed by pyrolysis of 2 at 1000 °C: Osterodt, J.; Zett, A.; Vögtle, F. Tetrahedron 1996, 52, 4949-4962.
13. 6) Yafuso, M.; Van, C.F.; Hui, H.K.; Miller, W.W. Europ. Patent 0243116 (1987); Chem. Abstr. 1988, 109, P34837.
14. 6) Yafuso, M.; Van, C.F.; Hui, H.K.; Miller, W.W. Europ. Patent 0243116 (1987); Chem. Abstr. 1988, 109, P34837.
15. 7) Kubo, T.; Yamamoto, K.; Nakasuji, K.; Takui, T.; Murata, I. Angew. Chem. 1996, 108, 456-457; Angew. Chem. Int. Ed. Engl. 1996, 35, 439-441.
16. 7) Kubo, T.; Yamamoto, K.; Nakasuji, K.; Takui, T.; Murata, I. Angew. Chem. 1996, 108, 456-457; Angew. Chem. Int. Ed. Engl. 1996, 35, 439-441.
17. 1JC-H = 126 Hz); assignments by DEPT and gated decoupling).
18. -3. Atomic coordinates and e.s.d.'s have been deposited at the Cambridge Crystallographic Data Centre.
19. -3. Atomic coordinates and e.s.d.'s have been deposited at the Cambridge Crystallographic Data Centre.
20. 10) Ro, D.M.; Pascal, Jr., R.A. Chem. Mater. 1993, 5, 1358-1361.
21. -1; non-bonded cutoff: 8 Å.
22. 2, 400 MHz) did not show a splitting for the singlet at δ = 1.66 of the t-butyl groups and for other signals at - 90 °C.
23. 13) Packing coefficient of 4: 0.644 (2: 0.825). Van der Waals radii used: C, 1.80 Å; H, 1.17 Å. Close-packing was found to dominate the crystallisation of large polycyclic aromatic hydrocarbons: Goddard, R.; Haenel, M.W.; Herndon, W.C.; Krüger, C.; Zander, M. J. Am. Chem. Soc. 1995, 117, 30-41.
24. 14) Dziewonski, K. Chem. Ber. 1903, 36, 962-971.
25. 15) Illingworth, E.; Peters, A.T. J. Chem. Soc. 1951, 1602-1607.
26. 3, 300 K, 150 MHz, TMS): S = {147.58, 147.55, 147.51, 147.49}, {138.37, 138.36, 138.34, 138.33}, {136.01, 136.00, 135.98, 135.97}, {135.76, 135.68, 135.57, 135.48}, {135.48, 135.46, 135.45}, {135.09, 135.01, 134.91, 134.82}, {129.21, 129.20, 129.18}, {126.72, 126.69, 126.67, 126.64}, {126.27 126.25), 124.46 (br.), {123.26, 123.24, 123.22, 123.19}, {122.45, 122.43, 122.41, 122.39}, 36.50, 32.65. Brackets indicate the closely attached lines, see text. We thank Dr. R. Mynott and Mrs. C. Wirtz for the NMR measurements and their help interpreting the spectra.
27. 17) Kovacic, P.; Jones, M.B. Chem. Rev. 1987, 87, 357-379.
28. 18) Müller, M.; Mauermann-Düll, H.; Wagner, M.; Enkelmann, V.; Müllen, K. Angew. Chem. 1995, 107, 1751-1754; Angew. Chem. Int. Ed. Eng. 1995, 34, 1583-1586.
29. 18) Müller, M.; Mauermann-Düll, H.; Wagner, M.; Enkelmann, V.; Müllen, K. Angew. Chem. 1995, 107, 1751-1754; Angew. Chem. Int. Ed. Eng. 1995, 34, 1583-1586.
30. 19) Deubzer, B.; Fischer, E.O.; Fritz, H.P.; Kreiter, C.G.; Kriebitzsch, N.; Simmons, Jr., H.D.; Willeford, Jr., B.R. Chem. Ber. 1967, 100, 3084-3096.
31. 3].