A New Approach to the Ring Opening Reactions of 2,7,7-Trimethyl-3,3-dibromotricyclo[4.1.1.02,4]octane

The reaction of a-pinene and dibromocarbene produced a fairly unstable product, 2,7,7-trimethyl-3,3-dibromotricyclo[4.1.1.02,4]octane, from which 3-bromo-7,7-dimethyl-2-methylenebicyclo[4,1,1]oct-3-ene and 3-bromo-2,7,7-trimethylbicyclo [4,1,1]octa-2,4-diene were obtained in chloroform at room temperature and in various other media and conditions. Two new compounds, 3-bromo-2,7,7-trimethylbicyclo [4.1.1]oct-3-en-2-ol and 2-(4-bromo-5-methylcyclohepta-3,5-dien-1-yl) propan-2-ol, were observed in aqueous acetone in addition to the previous two. The stability and formation mechanism of the formed products are discussed

A New Approach to the Ring Opening Reactions of 2,7,7-Trimethyl-3,3-dibromotricyclo[4.1.1.02,4]octane

The reaction of a-pinene and dibromocarbene produced a fairly unstable product, 2,7,7-trimethyl-3,3-dibromotricyclo[4.1.1.02,4]octane, from which 3-bromo-7,7-dimethyl-2-methylenebicyclo[4,1,1]oct-3-ene and 3-bromo-2,7,7-trimethylbicyclo [4,1,1]octa-2,4-diene were obtained in chloroform at room temperature and in various other media and conditions. Two new compounds, 3-bromo-2,7,7-trimethylbicyclo [4.1.1]oct-3-en-2-ol and 2-(4-bromo-5-methylcyclohepta-3,5-dien-1-yl) propan-2-ol, were observed in aqueous acetone in addition to the previous two. The stability and formation mechanism of the formed products are discussed

___

  • E.V. Dehmlow, In Houben-Weyl Methoden der Organischen Chemie; M. Regitz, Ed.; Georg Thieme Verlag: Stuttgart, Vol. E19, Part 2, pp 1467-1505, 1521-1600, 1608-1622 and 1625-1627, Germany, 1989.
  • A. Jonczyk and M. Fedorynski, M. In Houben-Weyl Methods of Organic Chemistry; A. De Meijere, A., Ed., Georg Thieme Verlag: Vol. E17a, pp 589-734, Stuttgart, Germany, 1997.
  • R.R Kostikov, A.P. Molchanov and H. Hopf, Top. Curr. Chem. 155, 41, (1990).
  • M.G. Banwell and M.E. Reum, Advances in Strain in Organic Chemistry; Vol. 1, p 19. JAI Press: London, 1991.
  • M. Fedorynski, Chem Rev. 103, 1099-1132 (2003).
  • K.B. Wiberg, In The Chemistry of Functional Groups, The Chemistry of the Cyclopropyl Group, Z. Rappoport, Ed.; Wiley: New York, p 1. 1987.
  • D. Cremer, E. Kraka and K.J. Szabo, K. In The Chemistry of Functional Groups, The Chemistry of the Cyclopropyl Group, Vol. 2, Z. Rappoport, Ed.; p 43, Wiley: Chichester, U.K., 1995.
  • 8. L.A. Wessjohann, A. Ludger, A. Muhlbauer and U. Sinks, Acta Chem. Scan. 51, 1112-1115 (1997).
  • 9. M.G. Banwell and C.J. Cowdenle, Austr. J. Chem. 47, 2235-54 (1994).
  • 10. D.G. Lindsay and C. B. Reese, Tetrahedron 21, 1673-80, (1965).
  • D. Wege, J. Org. Chem. 55, 1667-1670, (1990).
  • K. Kitahonoki, Y. Takano, A. Matsuura and K. Kotera, Tetrahedron 25, 335-353 (1969).
  • F. T¨umer, Y. Taskesenligil and M. Balci, J. Org. Chem. 66, 3806-3810, (2001).
  • F. Algı, T. H¨okelek and M. Balcı, J. Chem. Res. (S), 658-660, (2004).
  • J. Hatem and B. Waegell, Tetrahedron Lett. 23, 2069-2072 (1971).
  • J. Graefe, Q.T. Lam and M. Muehlstaedt, Z. Chem. 11, 252-3, (1971).
  • J. Hatem and B. Waegell, Tetrahedron Lett. 23, 2019-2022 and 2023-2026, (1973).
  • J. Hatem and B. Waegell, Tetrahedron, 46, 2789-2806 (1990).
  • For isolation and further reactions of 11 see: M.S. Baird, P. Mark, H. J. Sadler, J.P. Zahra and B. Waegell, J.
  • Chem. Soc. Chem. Commun. 452-453 (1979).
  • A. Azizoglu, R. Ozen, T. Hokelek and M. Balci, J. Org. Chem. 69, 1202-1206, (2004).
Turkish Journal of Chemistry-Cover
  • ISSN: 1300-0527
  • Yayın Aralığı: Yılda 6 Sayı
  • Yayıncı: TÜBİTAK
Sayıdaki Diğer Makaleler

Analysis of the Essential Oil Composition of Sideritis albiflora Using Direct Thermal Desorption and Headspace GC-MS Techniques

Gülaçtı TOPÇU, Aslı BARLA, Ahmet C. GÖREN

The Effect of Silane Modification on the Adsorptive Properties of Natural Pyrophyllite and Synthetic Titanium-Based Powders Prepared by the Sol-Gel Process

Şadiye ŞENER, Murat ERDEMOĞLU, Meltem ASİLTÜRK

Development of Gold Porous Plate Electrode and Examination of Its Performance for Iodine Determination

Ülkü Anık KIRGÖZ, Hüseyin TURAL

The Electroanalytical Determination of Sodium Borohydride Using a Gold Electrode

Hüseyin ÇELİKKAN, Hasan AYDIN, M. Levent AKSU

Miscibility of Methylmethacrylate-co-methacrylic Acid Polymer with Magnesium, Zinc, and Manganese Sulfonated Polystyrene Ionomers

Cemil ALKAN, Nebahat YURTSEVEN, Leyla ARAS

Triterpene Saponins from Nigella sativa L.

Mustafa Kemal TAŞKIN, Özgen Alankuş ÇALIŞKAN, Hüseyin ANIL, Hassan ABOU-GAZAR, Ikhlas A. KHAN, Erdal BEDİR

Polyphenolic Compounds and Antimicrobial Activity of Quercus aucheri Leaves

M. Koray SAKAR, Didem ŞÖHRETOĞLU, Meral ÖZALP

Voltammetric, UV Absorption and Viscometric Studies of the Interaction of Norepinephrine with DNA

Mehmet ASLANOĞLU, Necla ÖGE

Selective oxidation of thiols to disulfides catalyzed by iron (III)-tetra phenyl porphrin using urea-hydrogen peroxide as oxidizing reagent

Majid MOGHADAM, Morteza MONTAZEROZOHORI, Mohammad Hosein HABIBI, Khodabakhsh NIKNAM, Bahador KARAMI

Excellent and convenient procedures for reduction of benzene and its derivaties

Aliye ALTUNDAŞ, Melek KARAKAYA, Abdullah MENZEK, Demirci Demet GÜLTEKİN