Reaction of cycloheptatriene derivatives with 1,3-diketones in the presence of $Mn(OAc)_3$

Reaction of cycloheptatriene derivatives with 1,3-diketones in the presence of $Mn(OAc)_3$

The reactions of some 1,3-dicarbonyl compounds with cycloheptatriene derivatives in the presence of $Mn(OAc)_3$ were examined. Cycloheptatriene forms mainly [2+3] and [6+3] dihydrofuran addition products derived from cycloheptatriene. However, the reaction of acetylacetone with cycloheptatriene substituted with an electron withdrawing group exclusively gave products derived from the norcaradiene structure. The formation mechanism of the products as well as the role of the substituent attached to cycloheptatriene is discussed.

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  • 1. (a) McNamara, O. A.; Maguire, A. R. Tetrahedron, in press, doi: 10.1016/j.tet.2010.10.030. (b) Balci, M. Turk. J. Chem. 1992, 16, 42-90. (c) Le Noble, W. J. “Highlights of Organic Chemistry” Marcel Dekker, Inc. New York 1974, 402. (d) Maier, G. Angew Chem. Intern. Edit. Engl. 1967, 6, 402-413.
  • 2. Hoffmann, R., Tetrahedron Lett. 1970, 2907-2909.
  • 3. Günter. H., Tetrahedron Lett. 1970, 5173-5176.
  • 4. Tang, T. H.; Lew, C. S. Q.; Cui, Y. P.; Capon, B.; Csizmadia, I. G. J. Mol. Struct. (THEOCHEM) 1994, 111, 149-164.
  • 5. (a) Adam, W.; Balci, M. Angew. Chem. 1978, 90, 1014-1016. Angew. Chem. Intern. Edit. Engl. 1978, 17, 954-955. (b) Adam,W.; Balci, M.; Pietrzak, B. J. Am. Chem. Soc. 1979, 101, 6285-6291. (c) Adam, W.; Balci, M. J. Org. Chem. 1979, 44, 1189-1190. (d) Balci, M., Atasoy, B. Tetrahedron Lett. 1984, 25, 4033- 4036. (e) Menzek, A.; Krawiec, M.; Watson, W. H.; Balci, M. J. Org. Chem. 1991, 56, 6755-6758. (f) Menzek, A.; Balci, M. Tetrahedron. 1993, 58, 6071- 6078.) (g) Menzek, A.; Balci, M. Austr. J. Chem. 1993, 46, 1613-1621. (h) Sengul, M. E.; Ceylan, Z.; Balci, M. Tetrahedron, 1997, 53, 8522-8532. (i) Saracoglu, N.; Menzek, A.; Sayan, S.; Salzner, U.; Balci, M. J. Org. Chem. 1999, 64, 6670- 6676. (j) C¸ elik, M.; Balci, M. Arkivoc, 2007, XIII, 150-162.
  • 6. (a) Hanamura, M.; Kamada, J.; Amano, A.; Takeuchi, K.; Okazaki, T.; Hirai, K.; Kitagawa, T. Eur. J. Org. Chem. 2010, 3257-3264, (b) Freccero, M.; Gandolfi, R.; Sarzi-Amade, M.; Bovio, B. Eur. J. Org. Chem. 2002, 569-579.
  • 7. (a) Bush, J. B.; Finkbeiner, H. J. Am. Chem. Soc. 1968, 90, 5903-5905. (b) Heiba, E. I.; Dessau, R. M.; Koehl, W. J. J. Am. Chem. Soc. 1968, 90, 5905-5907.
  • 8. For reviews on Mn(OAc) 3 oxidation see: (a) Demir, A. S.; Emrullahoglu, M. Curr. Org. Synth. 2007, 4 , 321-350. (b) Snider, B. B. Chem. Rev. 1996, 96, 339- 363. (b) Iqbal, J.; Bhatia, B.; Nayyar, N. K. Chem. Rev. 1994, 94, 519-564. (c) Melikyan, G. G. Synthesis 1993, 833-850.
  • 9. For dihydrofuran formation see: (a) Yilmaz, M.; Uzunalioglu, N.; Pekel, A. T. Tetrahedron 2005, 61, 8860-8867. (b) Huang, J. -W.; Shi, M. J. Org. Chem. 2005, 70, 3859-3863. (c) Nguyen, V. -H.; Nishino, H. Tetrahedron Lett. 2004, 45, 3373-3377.
  • 10. (a) Heiba, E. I.; Dessau, R. M. J. Am. Chem. Soc. 1971, 93, 524-527; (b) Heiba, E. I.; Dessau, R. M. J. Am. Chem. Soc. 1972, 94, 2888-2889; (c) Heiba, E. I.; Dessau, R. M. J. Am. Chem. Soc. 1974, 96, 7977-7981.
  • 11. (a) Ali, M. F. C¸alı¸skan, R.; S¸ahin, E.; Balcı, M. Tetrahedron 2009, 65, 1430- 1437. (b) C¸alı¸skan, R.; Ali, M. F.; S¸ahin, E.; Watson, W. H.; M. Balcı, J. Org. Chem. 2007, 72, 3353-3359; (c) C¸ali¸skan, R.; Pekel, T.; Watson, W. H.; Balci, M. Tetrahedron Lett. 2005, 46, 6227-6230.
  • 12. Betz, W.; Daub, J. Chem. Ber. 1972, 10, 1778-1779.
  • 13. Balci, M. Basic 1 H- and 13C-NMR Spectroscopy, Elsevier, 2005.
  • 14. (a) Altundas, A.; Akbulut, N.; Balci, M. Helv. Chim. Acta 1998, 81, 828-836. (b) Balci, M.; Atasoy, B. Tetrahedron Lett. 1984, 25, 4033-4036. (c) Saba, A.; De Lucchi, O. Heterocycles 1987, 26, 2339-2342. (d) Mori, A.; Takeshita, H. Chem. Lett. 1978, 395-396. (e) Asao, T.; Yagihara, M.; Kitahara, Y. Bull. Chem. Soc. Jpn. 1978, 51, 2131-2135.
  • 15. Fleming, I. Frontier Orbitals and Organic Chemical Reactions, John Wiley & Sons, Ltd. 1976.
Turkish Journal of Chemistry-Cover
  • ISSN: 1300-0527
  • Yayın Aralığı: Yılda 6 Sayı
  • Yayıncı: TÜBİTAK
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