Journals / Turkish Journal of Chemistry / 2003 / Cilt: 27 - Sayı: 3

Bromination of 1-cyclopent-1-en-1-ylbenzene and 1-(5-bromocyclopent-1-en-1-yl) benzene and theoretical ınvestigation of the products

Pages
287–294
Publication Date
2022-11-04
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 of 11 was explained by the formation of a weakly bridged bromoniun ion of type 9.

📌 3 Key Takeaways

🎯
Objective & Hypothesis:The bromination of 1-cyclopent-1-en-1-ylbenzene (4) in different solvents and at different temperatures was accompanied by the evolution of hydrogen bromide and yielded 1-(5-bromocyclopent-1-en-1-yl)benzene (8).
📊
Key Findings & Data:Further bromination of 8 gave exclusively 2R(S),5R(S)-1-(1,2,5-tribromocyclopentyl)benzene (11).
💡
Conclusion & Impact:The formation of 11 was explained by the formation of a weakly bridged bromoniun ion of type 9.
🔬Design:Research Article
📍Scope:Comprehensive Sample
⚙️Variables:Domain Parameters

Abstract

The bromination of 1-cyclopent-1-en-1-ylbenzene (4) in different solvents and at different temperatures was accompanied by the evolution of hydrogen bromide and yielded 1-(5-bromocyclopent-1-en-1-yl)benzene (8). Further bromination of 8 gave exclusively 2R(S),5R(S)-1-(1,2,5-tribromocyclopentyl)benzene (11). The experimental results were compared with the theoretical ones based on semi-empirical (MM+ and AM1), Hartree-Fock (HF) and density functional theory (DFT). The formation of 11 was explained by the formation of a weakly bridged bromoniun ion of type 9.

🔖

Cite This Article

CEYLAN, M., KINAL, A., BALCI, M., SÜTBEYAZ, Y. (2022). Bromination of 1-cyclopent-1-en-1-ylbenzene and 1-(5-bromocyclopent-1-en-1-yl) benzene and theoretical ınvestigation of the products. Turkish Journal of Chemistry, Cilt: 27 - Sayı: 3, 287–294. https://ajindex.com/articles/602260

📄 Full Text PDF Viewer

📄

PDF görüntüleyici hazırlanıyor...

References (11)

  1. a) M. Balci, and Y. Taskesenligil, In B. Halton, (Ed), Advances in Strained and Interesting Organic Molecules, Vol. 8, JAI Press Inc. 2000, pp 43-81. b) R.P. Johnson, Chem. Rev., 89 1111-1124 (1989)
  2. For most recent papers see: a) R. Özen, and M. Balci, Tetrahedron, 58, 3079-3083 (2002). b) S. Drinkuth, S. Groetsch, E-M. Peters, K. Peters, and M. Christl, Eur. J. Org. Chem., 2665-2670 (2001). c) M. Fernandez-Zertuche, R. Hernandez-Lamoneda, and A. Ramirez-Solis, J. Org. Chem. 65, 5207-5211 (2000). d) M. Christl, and S. Groetsch, Eur. J. Org. Chem., 1871-1874 (2000). e) S. Groetsch, J. Spuziak, and M. Christl, Tetrahedron, 56, 4163-4171 (2000). f) M. Nendel, L. M. Tolbert, L.A. Herring, N.M. Islam, and K.N. Houk, J. Org. Chem., 64 976-983 (1999)
  3. F. Algi, R. Özen, and M. Balci, Tetrahedron Lett., 43, 3129-3131 (2002)
  4. A.E. Favorskii, J. Gen. Chem. USSR (Engl. Transl.), 6 720-726 (1936)
  5. G. Wittig, and J. Heyn, Justus Liebigs Ann. Chem., 756, 1-9 (1972). 6. a) L.K. Montgomery, F. Scardiglia, and J.D. Roberts, J. Am. Chem. Soc., 87, 1917-1925 (1965). b) L.K. Montgomery, and L.E. Applegate, J. Am. Chem. Soc., 89, 2952-2960 (1967)
  6. C.H. DePuy, G.F. Morris, J.S. Smith, and R.J. Smat, J. Am. Chem. Soc., 87, 2421-2428 (1965). 8. a) M.F. Ruasse, Advances in Physical Organic Chemistry, Academic Press, 28, 207-291 (1993). b) I.Roberts, G.E. Kimbal, J. Am. Chem. Soc., 59, 947-955 (1937)
  7. P.L. Barili, G. Bellucci, F. Marioni, I. Morelli, and V. Scartoni, J. Org. Chem., 38, 3472-3478 (1973)
  8. M.J. Frisch, G.W. Trucks, H.B. Schlegel, G.E. Scuseria, M.A. Robb, J.R. Cheeseman, V.G. Zakrzewski, J.A. Montgomery, Jr., R.E. Stratmann, J.C. Burant, S. Dapprich, J.M. Millam, A.D. Daniels, K.N. Kudin, M. C. Strain, O. Farkas, J. Tomasi, V. Barone, M. Cossi, R. Cammi, B. Mennucci, C. Pomelli, C. Adamo, S. Clifford, J. Ochterski, G.A. Petersson, P.Y. Ayala, Q. Cui, K. Morokuma, D.K. Malick, A.D. Rabuck, K. Raghavachari, J.B. Foresman, J. Cioslowski, J.V. Ortiz, A.G. Baboul, B.B. Stefanov, G. Liu, A. Liashenko, P. Piskorz, I. Komaromi, R. Gomperts, R.L. Martin, D.J. Fox, T. Keith, M.A. Al-Laham, C.Y. Peng, A. Nanayakkara, M. Challacombe, P.M.W. Gill, B. Johnson, W. Chen, M.W. Wong, J.L. Andres, C. Gonzalez, M. Head-Gordon, E.S. Replogle, and J.A. Pople, Gaussian 98, Revision A.8, Gaussian, Inc., Pittsburgh PA, 1998
  9. F. Jensen, Introduction to Computational Chemistry, John Wiley & Sons, 1999
  10. A.D. Becke, J. Chem. Phys. 98, 5648 (1993)
  11. C. Lee, W. Y