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.

___

  • 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: 6
  • Yayıncı: TÜBİTAK
Sayıdaki Diğer Makaleler

Simple and rapid spectrophotometric determination of trace level chromium using bis (salicylaldehyde) orthophenylenediamine in nonionic micellar media

M. Jamaluddin AHMED, Najma MEMON, Rubina SOOMRO

Effect of CMC and HPC mixture on the photocatalytic activity of Nd-TiO2/SiO2 film under visible light irradiation

Parviz ABEROOMAND AZAR, Shahram MORADI DEHAGHI, Susan SAMADI

A Simple and Rapid Spectrophotometric Determination of Trace Level Simple and rapid spectrophotometric determination of trace level chromium using bis (salicylaldehyde) orthophenylenediamine in nonionic micellar media

Rubina SOOMRO, M. Jamaluddin AHMED and Najma MEMON, Najma MEMON

Azocalixarenes.7: Synthesis and study of the absorption properties of novel mono-azo substituted chromogenic calix[4]arenes

Özlem ÖZEN KARAKUŞ and Hasalettin DELİGÖZ

Simultaneous determination of trace Sn(II) and Sn(IV) using differential pulse polarography and application

Ülkü ÜNAL and Güler SOMER

Structural studies of complex compounds of 6,6'-diacetyl-2,2'-bipyridine dioxime with copper(I/II), platinum(II), and palladium(II) metal ions

Abdurrahman ŞENGÜL, Hakan AĞAÇ, Burak ÇOBAN and Erol EROĞLU

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

Mahir Burak SÜDEMEN, Mustafa ZENGİN, Hayriye GENÇ And

Synthesis and characterisation of tris(2,4-dinitrophenoxo)monooxovanadium(V) and its complex salts

Neeraj SHARMA, Reena SHARMA, Meena KUMARI And

Effect of CMC and HPC mixture on the photocatalytic activity of Nd-$TiO_2/SiO_2$ film under visible light irradiation

Parviz Aberoomand AZAR, Shahram Moradi DEHAGHI, Susan SAMADI, Mohammad Saber TEHRANI, Mohammad Hadi GIVIANRAD

Synthesis and biological activity of 5-substituted-2-amino-1,3,4-oxadiazole derivatives

Sanjeev KUMAR