Synthesis of alkoxy Meta-Terphenyls using Aryl- Grignards
Subject Areas : Chemistry and Chemical Engineering of all specializations
1 - Department of Chemistry, Male.C., Islamic Azad University, Malekan, Iran
Keywords: Aryl- Grignard, alkoxy Meta-Terphenyl, diphenyl benzene, tetrahydrofuran,
Abstract :
Considering the application of terphenyl ( di phenyl benzene ) derivatives in the synthesis of cyclophens, star polymers , liquid crystals, plastics, insulating materials, as well as the production of drugs, dyes, pesticides and fungicides, in this research work, we synthesized suitable precursors for the synthesis of phenol ' s ter phenyl derivatives and succeeded in preparing these precursors with an easy , low - cost and high - efficiency method. we prepared Grignard compound ( the aromatic part has an alkoxy group) on 2 , 6- di chloro iodo benzene in refluxing in tetra hydro furan, then hydrolyzing the intermediate formed , which is a suitable precursor for the mentioned cases. In this research we used metoxy group as alkoxy group in our compounds
In organic chemistry, the alkoxy group is used as a protecting group for some functional groups.
[1] Y.Sun,Y. Xu, Z.Sun, Ch.Wang,Y.Wei,Effect of stereo configure ation of aromatic ligands on retention and selectivity of terphenyl isomer-bonded stationary phases, Journal of
Chromatography A, 1698 (2023), 464005 [2]C. Sutradhar, W. Bae, S. Song, K. Joo, H. Na, J.Lee, W. Kim, H. Jang, Synthesis and characterization of fluoro sulfonyl imide-based poly(benzoyl diphenyl benzene) membranes for
proton exchange membrane fuel cells, Fuel , 390 (2025) , 15, 134741 [3] S. Krieck, R. Kretschmer, H. Gorls, M. Westerhauseh, Rubidium-mediated birch-type reduction of 1,2-Diphenylbenzene in tetrahydrofuran, Journal of the American Chemical Society, 18 (2011), 133, 6960–6963
[4] K. Goto, G. Yamamoto, B. Tan, R. Okazaki, A novel dendrimer-type m-terphenyl substituent
for the kinetic stabilization of highly reactive species, Tetrahedron letters, 42 (2001), 4875-4877 [5] O. J. Curnow, G. M. Fern, D. Wöll, Synthesis of the sterically constrained ligand precursor cyclopentadienyl-2,6-diphenylbenzene and structure of [(2,6-Ph2–C6H3-η5-C5H4)Zr(NEt2)3],
Inorganic Chemistry Communications, 9 (2003), 6, 9, 1201-1204 [6] D. Abeysekera, K. N. Robertson, T. S. Cameron, J. A. C. Clyburne, M-terphenyl-substituted amidinates: useful ligands in the preparation of robust aluminum alkyls, Organometallics, 20 (2001), 5532-5536
[7] B. S. Furniss, A. J. Hannaford, V. Rogers, P. W. G. Smith, A. R. Tatchel, Vogel’s Text Book of
practical Organic Chemistry, 4 th edition, Longman London and Newyork (1989) , 935-937 [8] Jayaram R. Tagat , Stuart W. McCombie, Beverly E. Barton, James J., and Jennifer Sh., Synthetic inhibitors of interleukin-6 II: 3,5-diaryl pyridines and meta-terphenyls , Bioorganic & Medicinal
Chemistry Letters, 18 (1995) , 2143-2146 [9] A.Kannan, P. Rajakumar, V. Kabaleeswaran, S.S. Rajan, Synthesis of cyclophanes with intra-
annular functionality and cage structure, J. Org. Chem., 61(1996), 5090 [10] P. Rajakumar, M. Srisailas, Meta-terphenyls as building blocks for
benzimidazolophanes, Tetrahedron letters, 30(1997), 5323-5326 [11] U. Luning, H. Baumgartner, C. Manthey, B. Meynhardt, Concave reagents. 20. Sterically shielded m-terphenyls as selective agents in General protonations, J. Org. Chem., 61(1996), 7922-
7926