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Synthesis 2008(5): 777-787  
DOI: 10.1055/s-2008-1032186
PAPER
© Georg Thieme Verlag Stuttgart · New York

Reactions of p-Benzoquinone with Sulfur Nucleophiles

Alan R. Katritzky*a, Dmytro Fedoseyenkoa, Prabhu P. Mohapatraa, Peter J. Steelb
a Center for Heterocyclic Compounds, Department of Chemistry, University of Florida, Gainesville, FL 32611-7200, USA
b Chemistry Department, University of Canterbury, Christchurch 8140, New Zealand
Fax: +1(352)3929199; e-Mail: katritzky@chem.ufl.edu;
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Publication History

Received 20 July 2007
Publication Date:
18 February 2008 (online)

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Reactions of p-Benzoquinone with Sulfur NucleophilesSynthesis 2012; 44(21): 3400-3400
DOI: 10.1055/s-0032-1316795

Abstract

The orientations of the reactions of p-benzoquinone with nucleophiles are discussed. The one-pot reaction of p-benzoquinone with alkanethiols gave the 2-, 2,6-, and 2,5-conjugate addition products. Novel 2,6- and 2,5-bis(alkylsulfanyl)-, 2,3,5-tris(alkylsulfanyl)-, and 2,3,5,6-tetrakis(alkylsulfanyl)-p-benzoquinones, and their corresponding hydroquinones, were obtained in good yields through a sequential addition/in situ oxidation protocol for further testing as polymerization inhibitors in rubber and petroleum products. The structures of five 2,5- and 2,6-disubstituted isomers were established by X-ray crystallography.

Key words

p-benzoquinone - thiols - conjugate additions - hydroquinones - polymerization inhibitors

    References

  • 1a Batenko NG. Karlivans G. Valters R. Chem. Heterocycl. Compd. (Engl. Transl.)  2005,  41:  691 
    CrossrefGoogle Scholar
  • 1b Lenaz G. Genova ML. Encyclopedia of Biological Chemistry, Vol. 3   Lennarz W. J. Lane M. D. Academic Press; New York: 2004.  p.621 
    CrossrefGoogle Scholar
  • 1c Aguilar-Martinez M. Macias-Ruvalcaba NA. Bautista-Martinez JA. Gomez M. Gonzalez FJ. Gonzalez I. Curr. Org. Chem.  2004,  8:  1721 
    CrossrefGoogle Scholar
  • 2a Vazquez C. Calabrese JC. Dixon DA. Miller JS. J. Org. Chem.  1993,  58:  65 
    Google Scholar
  • 2b Neilands O. Fizikas un Tehnisko Zinatnu Serija  1981,  63 
    Google Scholar
  • 3 Miyashita K. Imanishi T. Chem. Rev.  2005,  105:  4515 
    CrossrefGoogle Scholar
  • 4 Barrero AF. Alvarez-Manzaneda EJ. Mar Herrador M. Chahboun R. Galera P. Bioorg. Med. Chem. Lett.  1999,  9:  2325 
    CrossrefGoogle Scholar
  • 5 Loya S. Tal R. Kashman RY. Hizi A. Antimicrob. Agents Chemother.  1990,  34:  2009 
    CrossrefGoogle Scholar
  • 6 Bourguet-Kondraki ML. Longeon A. Morel E. Guyot M. Int. J. Immunopharmacol.  1991,  13:  393 
    CrossrefGoogle Scholar
  • 7 Farzaliev VM. Allakhverdiev MA. Shamkhalova SA. Rzaeva IA. Russ. J. Appl. Chem.  2004,  77:  783 
    CrossrefGoogle Scholar
  • 8 Parvez M. Mesher ST. Clark PD. Acta. Crystallogr., Sect. C  2000,  56:  574 
    CrossrefGoogle Scholar
  • 9 Adams RD. Miao S. Inorg. Chem.  2004,  43:  8414 
    CrossrefGoogle Scholar
  • 10a Katritzky AR. Odens HH. Voronkov MV. Rostek CJ. Maender OW. Rubber Chem. Technol.  2001,  74:  915 
    CrossrefGoogle Scholar
  • 10b Maender OW, Rostek CJ, Katritzky AR, Odens HH, and Voronkov MV. inventors; WO  2002046149.  ; Chem. Abstr. 2002, 137, 21378
    Crossref
  • 11a Carreno MC. Garcia RJL. Toledo MA. Chem. Eur. J.  2000,  6:  288 
    Google Scholar
  • 11b Grennberg H. Gogoll A. Backvall J.-E. J. Org. Chem.  1991,  56:  5808 
    Google Scholar
  • 12a Schmidt A. Mordhorst T. ARKIVOC  2003,  (xiv):  233 
    CrossrefGoogle Scholar
  • 12b Catalan J. Fabero F. Guijarro MS. Claramunt RM. Santa Maria MD. Foces-Foces M. de la C. Cano FH. Elguero J. Sastre R. J. Am. Chem. Soc.  1990,  112:  747 
    CrossrefGoogle Scholar
  • 12c Ballesteros P. Claramunt RM. Escolastico C. Maria MDS. J. Org. Chem.  1992,  57:  1873 
    CrossrefGoogle Scholar
  • 13 Escolastico C. Santa Maria MD. Claramunt RM. Jimeno ML. Alkorta I. Foces-Foces C. Cano FH. Elguero J. Tetrahedron  1994,  50:  12489 
    CrossrefGoogle Scholar
  • 14 Marxer A. Helv. Chim. Acta  1955,  38:  1473 
    CrossrefGoogle Scholar
  • 15 Zhang S.-L. Huang Z.-S. An L.-K. Bu X.-Z. Ma L. Li Y.-M. Chan ASC. Gu L.-Q. Org. Lett.  2004,  6:  4853 
    CrossrefGoogle Scholar
  • 16 Zhang S.-L. Huang Z.-S. Shen Y.-D. Li Y.-M. Yao J.-H. Huang M. Chan ASC. Gu L.-Q. Tetrahedron Lett.  2006,  47:  6757 
    CrossrefGoogle Scholar
  • 17a Ling T. Poupon E. Rueden EJ. Kim SH. Theodorakis EA. J. Am. Chem. Soc.  2002,  124:  12261 
    Google Scholar
  • 17b Knapp S. Myers DS. J. Org. Chem.  2002,  67:  2995 
    Google Scholar
  • 17c Yadav JS. Reddy BVS. Swamy T. Ramireddy N. Synthesis  2004,  1849 
    Google Scholar
  • 17d Tandon VK. Yadav DB. Singh RV. Vaish M. Chaturvedi AK. Shukla PK. Bioorg. Med. Chem. Lett.  2005,  15:  3463 
    Google Scholar
  • 17e Nishiyama T. Sugimoto T. Andoh Y. Polym. Degrad. Stab.  2001,  74:  189 
    Google Scholar
  • 17f Lowik DWPM. Tisi LC. Murray JAH. Lowe CR. Synthesis  2001,  1780 
    Google Scholar
  • 17g Tolstikov GA. Shul’ts EE. Mukhametyanova TS. Spirikhin LV. Zh. Org. Khim.  1991,  27:  273 
    Google Scholar
  • 17h Crescenzi O. Prota G. Schultz TM. Wolfram LJ. Gazz. Chim. Ital.  1990,  120:  21 
    Google Scholar
  • 17i Hanzlik RP. Weller PE. Desai J. Zheng J. Hall LR. Slaughter DE. J. Org. Chem.  1990,  55:  2736 
    Google Scholar
  • 17j Rudorf W.-D. G unther E. Augustin M. Tetrahedron  1984,  40:  381 
    Google Scholar
  • 17k Huang S.-T. Kuo H.-S. Hsiao C.-L. Lin Y.-L. Bioorg. Med. Chem.  2002,  10:  1947 
    Google Scholar
  • 17l Borokov VV. Evstigneeva RP. Mirakova EV. Rozynov BV. Khim. Geterotsikl. Soedin.  1991,  1419 
    Google Scholar
  • 18 Becker JY. Bernstein J. Bittner S. Harlev E. Sarma JARP. Shaik SS. New J. Chem.  1988,  12:  875 
    Google Scholar
  • 19a Yadav JS. Reddy BVS. Swamy T. Tetrahedron Lett.  2003,  44:  9121 
    CrossrefGoogle Scholar
  • 19b Yadav JS. Reddy BVS. Swamy T. Synthesis  2004,  106 
    CrossrefGoogle Scholar
  • 19c Jurd L. Aust. J. Chem.  1980,  33:  1603 
    CrossrefGoogle Scholar
  • 19d Singh PK. Rohtagi BK. Khanna RN. Synth. Commun.  1992,  22:  987 
    CrossrefGoogle Scholar
  • 19e Itahara T. J. Org. Chem.  1985,  50:  5546 
    CrossrefGoogle Scholar
  • 20a Musso H. Angew. Chem., Int. Ed. Engl.  1963,  2:  723 ; Angew. Chem. 1963, 75, 965
    Google Scholar
  • 20b Mueller P. Venakis T. Eugster CH. Helv. Chim. Acta  1979,  62:  2350 
    Google Scholar
  • 20c Knoevenagel E. Bueckel C. Ber. Dtsch. Chem. Ges.  1901,  34:  3993 
    Google Scholar
  • 21 Rozeboom MD. Tegmo-Larsson I. Houk KN. J. Org. Chem.  1981,  46:  2338 
    CrossrefGoogle Scholar
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These data can be obtained free of charge from the Cambridge Crystallographic Data Centre via www.ccdc.cam.ac.uk/data_request/cif.