SavedAdd your journal

Journals / Turkish Journal of Chemistry / 2011 / Cilt: 35 - Sayı: 1

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

Mustafa ZENGİN
Metin BALCI
Hayriye GENC
Mahir Burak SÜDEMEN
Pages
1–11
Publication Date
2022-11-05
DOI
—
🏛️Bibliographic metadata and full text access for this article are provided via DergiPark.
DergiPark Record ↗
✨

AI Summary & Key Takeaways

AI Insight
⚡ TL;DR(Too Long; Didn't Read)

The formation mechanism of the products as well as the role of the substituent attached to cycloheptatriene is discussed.

📌 3 Key Takeaways

🎯
Objective & Hypothesis:The reactions of some 1,3-dicarbonyl compounds with cycloheptatriene derivatives in the presence of $Mn(OAc)_3$ were examined.
📊
Key Findings & Data:Cycloheptatriene forms mainly [2+3] and [6+3] dihydrofuran addition products derived from cycloheptatriene.
💡
Conclusion & Impact:The formation mechanism of the products as well as the role of the substituent attached to cycloheptatriene is discussed.
🔬Design:Research Article
📍Scope:Comprehensive Sample
⚙️Variables:Domain Parameters

Abstract

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.

🔖

Cite This Article

ZENGİN, M., BALCI, M., GENC, H., SÜDEMEN, M. B. (2022). Reaction of cycloheptatriene derivatives with 1,3-diketones in the presence of $Mn(OAc)_3$. Turkish Journal of Chemistry, Cilt: 35 - Sayı: 1, 1–11. https://ajindex.com/articles/602097

📄 Full Text PDF Viewer

📄

PDF görüntüleyici hazırlanıyor...

References (1)

  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)