Synthesis 2015; 47(20): 3207-3211
DOI: 10.1055/s-0034-1380439
paper
© Georg Thieme Verlag Stuttgart · New York

A Facile and Selective Procedure for Oxidation of Hydroquinones using Silica Gel Supported Catalytic Cerium(IV) Ammonium Nitrate

Mohammed Hashmat Ali*
Department of Chemistry, Southeast Missouri State University, One University Plaza, Cape Girardeau, MO 63701, USA   Email: mhali@semo.edu
,
Andrea Welker
Department of Chemistry, Southeast Missouri State University, One University Plaza, Cape Girardeau, MO 63701, USA   Email: mhali@semo.edu
,
Crystal York
Department of Chemistry, Southeast Missouri State University, One University Plaza, Cape Girardeau, MO 63701, USA   Email: mhali@semo.edu
› Author Affiliations
Further Information

Publication History

Received: 26 April 2015

Accepted after revision: 15 May 2015

Publication Date:
09 July 2015 (online)


Abstract

A new procedure for oxidation of hydroquinones to quinones using a silica gel supported cerium(IV) ammonium nitrate-NaBrO3 reagent has been developed. This simple, easy to prepare and use, heterogeneous reagent is highly selective towards oxidation of 1,4-dihydroxybenzenes and produces high yields of quinones. Waste generated by using this procedure is minimal.

Supporting Information

 
  • References

  • 1 Handbook of Reagents for Organic Synthesis, Oxidizing, and Reducing Agents. Vol. 2. Burke SD, Danheiser RL. Wiley; New York: 1999
  • 2 Snyder CD, Rappoport H. J. Am. Chem. Soc. 1974; 96: 8046
  • 3 Vliet EB. Org. Synth., Coll. Vol. I 1941; 482
  • 4 Amati A, Dosualdo G, Zhao L, Bravo A, Fontana F, Minisci F, Bjorsvik H.-R. Org. Process Res. Dev. 1998; 2: 261
  • 5 Jempty TC, Gogins KA. Z, Mazur Y, Miller LL. J. Org. Chem. 1981; 46: 4545
  • 6 Billmann JH, Wolnak B, Barnes DK. J. Am. Chem. Soc. 1944; 66: 652
  • 7 Yu D, Mattern DL. Synth. Commun. 1999; 29: 821
  • 8 Fisher A, Henderson GN. Synthesis 1985; 641
  • 9 Tanoue Y, Terada A. Bull. Chem. Soc. Jpn. 1988; 61: 2039
  • 10 Ho T.-L, Hall TW, Wong CM. Chem. Ind. (London) 1972; 729
  • 11 Powell VH. Tetrahedron Lett. 1970; 3463
  • 12 Rao DV, Ulrich H, Sayigh AA. R. J. Org. Chem. 1975; 40: 2548
  • 13 Carrano MC, Ruano J.-LG, Urbano A. Synthesis 1992; 651
  • 14 Syper L, Klock K, Mlochowski J, Szulc Z. Synthesis 1979; 521
  • 15 Wang W, Breining T, Li T, Millburn R, Attardo G. Tetrahedron Lett. 1998; 39: 2459
  • 16 Radeke HS, Digits CA, Bruner SD, Snapper ML. J. Org. Chem. 1997; 62: 2823
  • 17 Tohma H, Morioka H, Harayama Y, Hashizume M, Kita Y. Tetrahedron Lett. 2001; 6899
  • 18 Knolker H.-J, Frohner W, Reddy KR. Synthesis 2002; 557
  • 19 Marchand AP, Alihodzic S, Shukla R. Synth. Commun. 1998; 28: 541
  • 20 Ali MH, Niedbalski M, Bohnert G, Bryant D. Synth. Commun. 2006; 36: 1751
  • 21 Jacob III P, Callery PS, Shulgin AT, Castagnoli NJr. J. Org. Chem. 1976; 41: 3627
  • 22 Wang W, Breining T, Li T, Milburn R, Attardo G. Tetrahedron Lett. 1998; 39: 2459
  • 23 Syper L, Kloc K, Mlochowski J, Szulc Z. Synthesis 1979; 521
  • 24 Chi S, Heathcock CH. Org. Lett. 1999; 1: 3
  • 25 Hayashi N, Yoshikaya T, Ohnuma T, Higuchi H, Sako K, Uekusa H. Org. Lett. 2007; 9: 5417
  • 26 Love BE, Duffy BC, Simmons A. Tetrahedron Lett. 2014; 55: 1994
  • 27 Morey J, Saa J.-M. Tetrahedron 1993; 49: 105
  • 28 Olah GA, Gupta BG. B, Fung AP. Synthesis 1980; 897
  • 29 Ganin E, Amer I. Synth. Commun. 1995; 25: 3149
  • 30 Hashemi MM, Beni YA. J. Chem. Res., Synop. 1999; 672
  • 31 Omura K. Synthesis 1998; 1145
  • 32 The Aldrich Library of 13C and 1H FT NMR Spectra. Pouchart C, Behnke J. Wiley; New York: 1993