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Synthetic Communications
An International Journal for Rapid Communication of Synthetic Organic Chemistry
Volume 41, 2010 - Issue 2
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Original Articles

Synthesis of p-Quinquephenyl from E,E-1,4-Bis(4-bromophenyl)-1,3-butadiene

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Pages 206-218 | Received 24 Jun 2009, Published online: 15 Dec 2010

REFERENCES

  • Stille , J. K. ; Gilliams , Y. Poly(p-phenylene) . Macromolecules 1971 , 4 , 515 – 517 .
  • (a) Ballard , D. G. H. ; Courtis , A. ; Shirley , I. M. ; Taylor , S. C. A biotech route to polyphenylene . J. Chem. Soc. Chem. Commun. 1983 , 954 – 955 ; (b) Ballard , D. G. H. ; Courtis , A. ; Shirley , I. M. ; Taylor , S. C. Synthesis of polyphenylene from a cis-dihydrocatechol, a biologically produced monomer . Macromolecules 1988 , 21 , 294 – 304 .
  • Unroe , M. R. ; Reinhardt , B. A. One-pot synthesis of p-polyphenyls via the intramolecular cyclization of 2-dimethylaminohex-5-en-1-ynes . Synthesis 1987 , 981 – 986 .
  • Baker , K. N. ; Fratini , A. V. ; Resch , T. , Knachel , H. C. ; Adams , W. W. ; Socci , E. P. ; Farmer , B. L. Crystal structures, phase transitions, and energy calculations of poly(p-phenylene) oligomers. Polymer 1993, 34, 1571–1587.
  • Takahashi , T. ; Tsai , F. U. ; Li , Y. A convenient preparative method of dibromoterphenyl and bis(bromophenyl)diene monomers using zirconacyclopentadienes . Chem. Lett. 1999 , 11 , 1173 – 1174 .
  • Annan , K. O. ; Scherf , U. ; Müllen , K. Visible-emitting poly[(3′,4′-dialkoxycarbonyl-2′-hydroxy-1,1′:5′,1″-terphenyl-4,4″-ylene)] . Synth. Met. 1999 , 99 , 9 – 16 .
  • Kadokawa , J. ; Suenaga , M. ; Kaneko , Y. Synthesis of poly(p-phenylene) having phthalic anhydride moieties in the main chain and its conversion into fluorescein derivative . Macromolecules 2008 , 41 , 3750 – 3754 .
  • Li , S. ; Li , Z. ; Fang , X. ; Chen , G. Q. ; Huang , Y. ; Xu , K. Synthesis and characterization of polyparaphenylene from cis-dihydrocatechol . J. Appl. Polym. Sci. 2008 , 110 , 2085 – 2093 .
  • Lohaus , H. Eine dien-synthese mit acetylen-dicärbonsaure-diäthylester . Ann. 1935 , 516 , 295 – 297 .
  • (a) McDonald , R. N. ; Campbell , T. W. Synthesis of hydrocarbon derivatives by the Wittig reaction, II: Diarylbutadienes and quinquephenyls . J. Org. Chem. 1959 , 24 , 1969 – 1975 ; (b) Campbell , T. W. ; McDonald , R. M. p-Quinquephenyl . Org. Synth. Coll. Vol. 1973 , 5 , 985 – 986 .
  • Fieser , L. F. ; Haddadin , M. Oxidative decarboxylation . J. Am. Chem. Soc. 1964 , 86 , 2392 – 2395 .
  • Courtot , P. ; Rumin , R. Photoisomérisation en série cyclohexadiénique-1,3, IV: Synthèse de dérivés cis et trans-disubstitués en 5,6 . Bull. Soc. Chim. Fr. 1969 , 3662 – 3665 .
  • Schuster , G. B. New chemiluminescent reaction systems: Light formation from the reaction of a vicinal diacid dichloride . J. Am. Chem. Soc. 1977 , 99 , 651 – 653 .
  • Ikeda , H. ; Takasaki , T. ; Takahashi , Y. ; Konno , A. ; Matsumoto , M. ; Hoshi , Y. ; Aoki , T. ; Suzuki , T. ; Goodman , J. L. ; Miyashi , T. The Photoinduced electron-transfer Cope rearrangments of 3,6-diaryl-2,6-octadienes and 2,5-diaryl-3,4-dimethyl-1,5-hexadienes: Stereospecificity and an unexpected formation of the bicyclo[2.2.0]hexane derivatives . J. Org. Chem. 1999 , 64 , 1640 – 1649 .
  • Perkin , W. H. On the formation of coumarin and of cinnamic and of other analogous acids from the aromatic aldehydes . J. Chem. Soc. 1877 , 31 , 388 – 427 .
  • Braun , J. V. ; Nelles , J. Synthese von zimtsäuren . Ber. 1933 , 66 , 1464 – 1470 .
  • Mikroyannidis , J. A. ; Spiliopoulos , I. K. ; Kasimis , T. S. ; Kulkarni , A. P. ; Jenekhe , S. A. Synthesis, photophysics, and electroluminescence of conjugated poly(p-phenylenevinylene) derivatives with 1,3,4-oxadiazoles in the backbone . Macromolecules 2003 , 36 , 9295 – 9302 .
  • Krauss , R. Ueber halogensubstitutionsproducte der α- und γ-truxillsäuren . Ber. 1904 , 37 , 216 – 224 .
  • Plevyak , J. E. ; Dickerson , J. E. ; Heck , R. F. Selective palladium-catalyzed vinylic substitutions with bromoiodo aromatics . J. Org. Chem. 1979 , 44 , 4078 – 4080 .
  • Wand , M. ; Thurmes , W. N. ; Moré , K. ; Vohra , R. T. High birefringence liquid crystal compounds. U.S. Patent 5,626,792, May 6, 1997 .
  • Malet , R. ; Moreno-Mañas , M. ; Parella , T. ; Pleixats , R. (1-Dimethylamino)-2-(diphenylphosphino)ethane)(3–1-arylallyl)palladium tetrafluoroborates: Preparation, isomeric equilibria, and correlations of NMR chemical shifts with Hammett substituent constants . J. Org. Chem. 1996 , 61 , 758 – 763 .
  • Couladouros , E. A. ; Soufli , I. C. ; Moutsos , V. I. ; Chadha , R. K. Total synthesis of combrestatins D . Chem. Eur. J. 1998 , 4 , 33 – 43 .
  • Bouziane , A. ; Hélou , M.; Bertrand Carboni, B.; Carreaux, F.; Demerseman, B. ; Bruneau , C. ; Renaud , J.-L. Ruthenium-catalyzed synthesis of allylic alcohols: Boronic acid as a hydroxide source . Chem. Eur. J. 2008 , 14 , 5630 – 5637 .
  • Demik , N. N. ; Kabachnik , M. M. ; Novikova , Z. S. ; Beletskaya , I. P. Palladium-catalyzed arylation of diethyl allylphophonate. Russ. J. Org. Chem. 1994, 30, 935–940.
  • Pastushak , N. O. ; Dombrovskii , A. V. Preparation of some unsaturated alkaryl aldehydes by reduction of nitriles of β-arylacrylic acids . Russ. J. Org. Chem. (Engl. Trans.) 1965 , 1 , 323 – 325 .
  • Parikh , J. R. ; Doering , W. V. E. Sulfur trioxide in the oxidation of alcohols by dimethyl sulfoxide . J. Am. Chem. Soc. 1967 , 89 , 5505 – 5507 .
  • Peyman , A. ; Uhlmann , E. ; Budt , K. ; Knolle , J. ; Winkler , I. ; Helsberg , M. Use of benzylphosphonic acid derivatives for the treatment of diseases caused by viruses. U.S. Patent 5,242,908, Sept. 7, 1993 .
  • Taylor , S. D. ; Kotoris , C. C. ; Dinaut , A. N. ; Chen , M.-J. Synthesis of aryl(difluoromethylenephosphonates) via electrophilic fluorination of α-carbanions of benzylic phosphonates with N-fluorobenzenesulfonimide . Tetrahedron 1998 , 54 , 1691 – 1714 .
  • Woodward , R. B. ; Hoffmann , R. The Conservation of Orbital Symmetry ; Verlag Chemie : Weinheim , 1970 .
  • Jain , P. C. ; Mukergee , Y. N. ; Anand , N. Novel aspects of the Diels–Alder reaction with 1,4- and 1,2-diphenylbutadienes under thermal and Lewis acid–catalyzed conditions . J. Am. Chem. Soc. 1974 , 96 , 2996 – 2997 .
  • Langler , R. F. Unambiguous assessments of reaction paths for selected pericyclic reactions . Química Nova 2000 , 23 , 703 – 705 .
  • Braun , J. V. ; Irmisch , G. ; Nelles , J. Synthesen in der di- und terphenylreihe II: Mitteil . Ber. 1933 , 66 , 1471 – 1483 .
  • France , H. ; Heilbron , I. M. ; Hey , D. H. Studies in the terphenyl series, part I: p-Terphenyl, nitro-, amino-, and halogeno-p-terphenyls . J. Chem. Soc. 1938 , 1364 – 1375 .
  • Müller , E. ; Töpel , T. Zur kenntnis des reaktiven verhaltens der organolithiumverbindungen . Ber. 1939 , 72 , 273 – 290 .
  • Kuivila , H. G. ; Keough , A. H. ; Soboczenski , E. J. Areneboronates from diols and triols . J. Org. Chem. 1954 , 19 , 780 – 783 .
  • Bowie , R. A. ; Musgrave , O. C. Organoboron compounds, part V: The hydrolysis of cyclic phenylboronates . J. Chem. Soc. 1963 , 3945 – 3949 .
  • Pickup , D. F. ; Yi , H. ; Iraqi , A. Preparation and properties of alternating 2,7-linked carbazole copolymers with phenylene units with varying number of fluorine substituents . J. Mat. Chem. 2009 , 44 , 3172 – 3178 .
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