Ring expansion of 11H-benzo[b]fluorene-11-methanols and related compounds leading to 17,18-diphenyldibenzo[a,o]pentaphene and related polycyclic aromatic hydrocarbons with extended conjugation and novel architectures

Tetrahedron

Volumn 62, Issue 18, 2006, Pages 4364-4371

  Yang, Yonghong ^a   Dai, Weixiang ^a   Zhang, Yanzhong ^a   Petersen, Jeffrey L ^a   Wang, Kung K ^a  

^a WEST VIRGINIA UNIVERSITY   (United States)

Author keywords

17,18 Diphenyldibenzo a,o pentaphene; 9 Fluorenylmethanols; Polycyclic aromatic hydrocarbons; Ring expansion; Wagner Meerwein rearrangement

Indexed keywords

17,18 DIPHENYLDIBENZO[A,O]PENTAPHENE; ANTHRACENE DERIVATIVE; BENZENE DERIVATIVE; METHANOL DERIVATIVE; PARAFORMALDEHYDE; PHENANTHRENE DERIVATIVE; POLYCYCLIC AROMATIC HYDROCARBON DERIVATIVE; UNCLASSIFIED DRUG;

ARTICLE; ARYLATION; CONJUGATION; POLYMERIZATION; PRIORITY JOURNAL; SYNTHESIS; WAGNER MEERWEIN REARRANGEMENT;

PUFFINUS AURICULARIS;

EID: 33646082273     PISSN: 00404020     EISSN: None     Source Type: Journal    
DOI: 10.1016/j.tet.2006.02.066     Document Type: Article

References (32)

1. Floyd A.J., Dyke S.F., and Ward S.E. Chem. Rev. 76 (1976) 509-562
2. Brown W.G., and Bluestein B. J. Am. Chem. Soc. 62 (1940) 3256-3257
3. Li H., Zhang H.-R., Petersen J.L., and Wang K.K. J. Org. Chem. 66 (2001) 6662-6668
4. Wang K.K., Zhang H.-R., and Petersen J.L. J. Org. Chem. 64 (1999) 1650-1656
5. Zhang H.-R., and Wang K.K. J. Org. Chem. 64 (1999) 7996-7999
6. Li H., Petersen J.L., and Wang K.K. J. Org. Chem. 66 (2001) 7804-7810
7. Yang Y., Petersen J.L., and Wang K.K. J. Org. Chem. 68 (2003) 5832-5837
8. Yang Y., Petersen J.L., and Wang K.K. J. Org. Chem. 68 (2003) 8545-8549
9. Dai W., Petersen J.L., and Wang K.K. Org. Lett. 6 (2004) 4355-4357
10. Han X., Zhang Y., and Wang K.K. J. Org. Chem. 70 (2005) 2406-2408
11. Schmittel M., Strittmatter M., Vollmann K., and Kiau S. Tetrahedron Lett. 37 (1996) 999-1002
12. Schmittel M., Strittmatter M., and Kiau S. Angew. Chem., Int. Ed. 35 (1996) 1843-1845
13. Schmittel M., Keller M., Kiau S., and Strittmatter M. Chem. Eur. J. 3 (1997) 807-816
14. Schmittel M., and Vavilala C. J. Org. Chem. 70 (2005) 4865-4868
15. Wang K.K. In: Krause N., and Hashmi A.S.K. (Eds). Modern Allene Chemistry Vol. 2 (2004), Wiley-VCH, Weinheim, Germany 1091-1126
16. Tinnemans A.H.A., and Laarhoven W.H. J. Chem. Soc., Perkin Trans. 2 (1976) 1115-1120
17. Tinnemans A.H.A., and Laarhoven W.H. J. Am. Chem. Soc. 96 (1974) 4617-4622
18. Chong J.M., Lajoie G., and Tjepkema M.W. Synthesis (1992) 819-820
19. Smith M.B., and March J. March's Advanced Organic Chemistry. 5th ed. (2001), Wiley-Interscience, New York 730-731
20. Tashiro M. Synthesis (1979) 921-936
21. Tashiro M., and Fukata G. Org. Prep. Proced. Int. 8 (1976) 51-74
22. Hofman P.S., Reiding D.J., and Nauta W.T.H. Recl. Trav. Chim. Pays-Bas 79 (1960) 790-793
23. Müller S., Liepold B., Roth G.J., and Bestmann H.J. Synlett (1996) 521-522
24. Myers A.G., Kuo E.Y., and Finney N.S. J. Am. Chem. Soc. 111 (1989) 8057-8059
25. Myers A.G., and Dragovich P.S. J. Am. Chem. Soc. 111 (1989) 9130-9132
26. Nagata R., Yamanaka H., Okazaki E., and Saito I. Tetrahedron Lett. 30 (1989) 4995-4998
27. Nagata R., Yamanaka H., Murahashi E., and Saito I. Tetrahedron Lett. 31 (1990) 2907-2910
28. Laarhoven W.H., Peters W.H.M., and Tinnemans A.H.A. Tetrahedron 34 (1978) 769-777
29. Vingiello F.A., Yanez J., and Campbell J.A. J. Org. Chem. 36 (1971) 2053-2056
30. Stiles M., and Miller R.G. J. Am. Chem. Soc. 82 (1960) 3802
31. Friedman L., and Logullo F.M. J. Am. Chem. Soc. 85 (1963) 1549
32. Kitamura T., Yamane M., Inoue K., Todaka M., Fukatsu N., Meng Z., and Fujiwara Y. J. Am. Chem. Soc. 121 (1999) 11674-11679