Synthetically Useful Aryl-Aryl Bond Formation via Grignard Generation and Trapping of Arynes. A One-Step Synthesis of p-Terphenyl and Unsymmetric Biaryls

Journal of Organic Chemistry

Volumn 50, Issue 17, 1985, Pages 3104-3110

  Hart, Harold ^a   Harada, Katsumasa ^a   Du, Chi Jen Frank ^a  

^a MICHIGAN STATE UNIVERSITY   (United States)

Author keywords

[No Author keywords available]

Indexed keywords

EID: 0000600868     PISSN: 00223263     EISSN: 15206904     Source Type: Journal    
DOI: 10.1021/jo00217a018     Document Type: Article

References (24)

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2. For more specialized reviews, see: Grimshaw, J.; deSilva, A. P. Chem. Soc. Rev. 1981, 10, 181. Kozhevnikov, I. V.; Matveer, K. I. Russ. Chem. Rev. (Engl. Transl.) 1978, 47, 649. Dhingra, O. P. in “Oxidation in Organic Chemistry, Part D.”; Trahanovsky, W. S., Ed.; Academic Press: New York, 1982, p 207. Ried, W.; Freitag, D. Angew. Chem. Int. Ed. Engl. 1968, 7, 835. Laarhoven, W. H. Recl. J. R. Neth. Chem. Soc. 1983, 102, 185, 241.
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7. (a) Sy, A.; Hart, H. J. Org. Chem. 1979, 44, 71. (b) Hart, H.; Lai, C.-Y.; Nwokogu, G.; Shamouilian, S.; Teuerstein, A.; Zlotogorski, C. J. Am. Chem. Soc. 1980, 102, 6649. (c) Hart, H.; Nwokogu, G. J. Org. Chem. 1981, 46, 1251. (d) Hart, H.; Shamouilian, S. J. Org. Chem. 1981, 46, 4874. (e) Hart, H.; Shamouilian, S.; Takehira, Y. J. Org. Chem. 1981, 46, 4427. (f) Hart, H.; Raju, N.; Meador, M. A.; Ward, D. L. J. Org. Chem. 1983, 48, 4357. (g) Hart, H.; Nwokogu, G. C. Tetrahedron Lett. 1983, 24, 5721. (h) Nwokogu, G. C.; Hart, H. Tetrahedron Lett. 1983, 24, 5725.
8. For a brief preliminary account, see: Hart, H.; Harada, K. Tetrahedron Lett. 1985, 26, 29.
9. The synthesis and chemistry of terphenyls is briefly reviewed by Cheeseman and Praill: Cheeseman, G. W. H.; Praill, P. F. G. In “Rodd's Chemistry of Carbon Compounds”, 2nd ed.; Elsevier: Amsterdam, 1974; Vol. III F, pp 51-57; MacBride, J. A. H. 1982 supplement; pp 322–323. Clar, E. “Polycyclic Hydrocarbons”; Academic Press: New York, 1964; Vol. 2, pp 221–223. p-Terphenyls see extensive use as liquid crystals, see: Saeva, F. D., Ed. “Liquid Crystals”; Marcel Dekker, Inc.: New York, 1979. (14) Fields, E. K. U.S. Patent 4 012 454, May 15, 1975. See also: Beilsteins “Handbuch der Organischen Chemie”, Hauptwerke Vol. 5, p 228, under 1,4-dibromo-x,x-diiodobenzene; the original reference mentioned there is unavailable to us. Aside from these, we can find no other references to 1.
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22. For 1, 2, 4-tribromobenzene: Derbyshire, D. H.; Waters, W. A. J. Chem. Soc. 1950, 573. For 3,4-dibromobiphenyl: Case, F. H.J. Am. Chem. Soc. 1936, 58, 1249.
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24. Baker, W.; Barton, J. W.; McOmie, J. F. W.; Penneck, R. J.; Watts, M. L. J. Chem. Soc. 1961, 3986. (41) It is essential to add the mixture to bromine and was not vice versa; when bromine was added to the reaction mixture, considerable 2-iodobiphenyl was formed, presumably as a consequence of oxidation of iodide to iodine by the added bromine. This was true regardless of how fast the bromine was added. Hence in this and all bromine quenches, the reaction mixture was added to excess bromine.