Excellent and convenient procedures for reduction of benzene and its derivaties

Excellent and convenient procedures for reduction of benzene and its derivaties

Reductions of benzene, toluene, ortho-xylene, cumene, anisole and benzoic acid to corresponding nonconjugated dienes were realized at room temperature by gas NH3 and Li. The reduced products were easily isolated because THF and dioxane were dissolved in the water. The yields and conversions of the reactions were 70-89% and 80-100%, respectively.

___

  • 1.H.O. House, Modern Synthetic Reactions; 2nd ed., W. A Benjamin, Los Angles, CA, pp 1-227, 1972.
  • 2.P.W. Rabideau, Tetrahedron 45, 1579-1603 (1989).
  • 3.M. Hudlicky, Reduction in Organic Chemistry; 2nd ed., ACS Monograph, 188, pp 61-79, 1996.
  • 4.A. Menzek, J. Chem. Educ. 79, 700-702 (2002).
  • 5.A.J. Birch and D. Nasipuri, Tetrahedron 6, 148-153, (1959).
  • 6.R.G. Harvey, Synthesis 161-172 (1970).
  • 7.J.M. Hook and L.N. Mander, Natural Prod. Rep. 3, 35-85 (1986).
  • 8.M. Balcı, Y. Sütbeyaz, and H. Seçen, Tetrahedron 46, 3715-3742 (1990).
  • 9.K.A. Powell, A.L. Hughes, H. Katchian, J.F. Jerauld and H.Z. Sable, Tetrahedron 28, 2019-2027 (1972).
  • 10.M. Mittelbach, N. Poklukar and H. Junek, Liebigs Ann. Chem. 2, 185-188 (1990).
  • 11.S. Spange, Prog. Polym. Sci. 25, 781-849 (2000).
  • 12.R.J. Giguere, A.M. Namen, B.O. Lopez, A. Arepally, D.E. Ramos, G. Majetich and J. Defauw, Tetrahedron Lett. 28, 6553-6556 (1987).
  • 13.M.S. Gültekin, E. Salama and M. Balcı, Carbohyd. Res. 338, 1615-1619 (2003).
  • 14.C.B. Wooster and K.L. Godfrey, J. Am. Chem. Soc. 59, 596-597 (1937).
  • 15.A.J. Birch, J. Chem. Soc, 430-446 (1944).
  • 16.A.L. Wilds and N.A. Nelson, J. Am. Chem. Soc. 75, 5360-5365 (1953).
  • 17.C.B. Wooster, U. S. Patent, 2182242 (1937).
  • 18.J.P. Wibaut and F.A. Haak, Recueil 67, 85-90 (1986).
  • 19.K.N. Campbell and J.P. McDermott, J. Am. Chem. Soc. 67, 282-283 (1945).
  • 20.A.P. Krapcho and A.A. Bothner, J. Am. Chem. Soc. 81, 3658-3666 (1959).
  • 21.L.H. Slaugh and J.H. Raley, J. Org. Chem. 32, 369-371 (1967).
  • 22.P.W. Rabideau and D.L. Huser, J. Org. Chem. 48, 4266-4271 (1983).
  • 23.A.W. Dumanski and A.W. Swerew, Chem. Zentr. Ill, 746 (1923).
  • 24.R.A. Benkeser, R.E. Robinson, D.M. Sauve and O.H. Thomas, J. Am. Chem. Soc. 77, 3230-3233 (1959).
  • 25.A.J. Birch, H.Q. Smith, Rev. Chem. Soc. 7, 17-33 (1958).
  • 26.R.A. Benkeser, J.A. Laugal and A. Rappa, Tetrahedron Lett. 25, 2089-2092 (1984).
  • 27.M.E. Grast, L.J. Dolby, S. Esfandiari, N.A. Fedoruk, N.C. Chamberlain and A.A. Avey, J. Org. Chem. 65,7098-7104 (2000).
  • 28.A. Menzek, A. Altundaş and D. Gültekin, J. Chem. Res-S., 752-753 (2003).
  • 29.M.E. Kuehne and B.F. Lambert, Org. Synth. Coll. Vol. 5, 400-403 (1973).
  • 30.W.E. Luttrell, Chem. Health Safe. 9(3), 30-31 (2002).
  • 31.W. Bajonowski, Int J Refrigeration £(1), 56-57 (1985).
  • 32.G.J. O'Kane, Anaesthesia 38(2), 1208-1213 (1983).
  • 33.P.J. Temple, D.S. Harper, R.G. Pearson and S.N. Linzon, Enviromental Pollution (1970-1979), 20(4),297-302 (1979).
  • 34.P.G. Urben, M.J. Pitt and L.A. Battle, Bretherick's Handbook of Reactive Chemical Hazards, 5nd ed.- Vol. 1, Butterworth Heimann Ltd, Oxford 0X2 8DP, 1553-1554, 1995.
Turkish Journal of Chemistry-Cover
  • ISSN: 1300-0527
  • Yayın Aralığı: 6
  • Yayıncı: TÜBİTAK
Sayıdaki Diğer Makaleler

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

Ülkü Anık KIRGÖZ, Hüseyin TURAL

Crystal structure of nitrato (2,2',2"-terpyridyl) platinum (II) hydrogen dinitrate, [Pt(terpy) $ONO_2$][$H(ONO_2)_2$]

Abdurrahman ŞENGÜL

Organotin (IV) derivaties of N-maleoylamino acids:Their synthesis and structural elucidation

Farhat HUMA, H. Moazzam BHATTI, Saqib ALI, Saira SHAHZADI

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

The Crystal and Molecular Structure of New Hydrogen Dinitrate of Nitrato(2,2',2''-terpyridyl)platinum(II) Ion, [Pt(terpy)ONO2][H(ONO2)2]

Crystal Structure Of NİTRATO(

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

Cemil ALKAN, Nebahat YURTSEVEN, Leyla ARAS

New Alkoxyzinc Salts Mediated Chemoselective Transesterification Reactions

Necdet COŞKUN, Mustafa ER

Selective Oxidation of Thiols to Disulfides Catalyzed by Iron(III) -- Tetra Phenyl Porphyrin Using Urea-Hydrogen Peroxide as Oxidizing Reagent

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

Excellent and convenient procedures for reduction of benzene and its derivaties

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

A new approach to the ring opening reactions of 2,7,7-trimethyl-3,3-dibromotricyclo[4.1.1.$0^{2,4}$] octane

Ömer ZAİM, Zekir ŞENOL, Metin BALCI