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Synthetic Communications
An International Journal for Rapid Communication of Synthetic Organic Chemistry
Volume 43, 2013 - Issue 16
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Original Articles

Nitrile-Promoted Alkene Epoxidation with Urea–Hydrogen Peroxide (UHP)

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Pages 2256-2264 | Received 09 Apr 2012, Published online: 03 Jun 2013

REFERENCES

  • Ihsan , E. In Comprehensive Heterocyclic Chemistry II ; Katritzky , A. R. ; Rees , C. W. ; Scriven , E. F. V. (Eds.); Pergamon : Oxford , 1996 ; pp. 97 – 144 .
  • Frank , W. C. Surprising stereoselectivity in the Payne epoxidation of terpinen-4-ol with acetonitrile/hydrogen peroxide . Tetrahedron: Asymmetry 1998 , 9 , 3745 – 3749 .
  • Asano , M. ; Nagasawa , C. ; Suzuki , M. ; Nishiyama , S. ; Sugai , T. Short-step and scalable synthesis of (±)-cytoxazone . Biosci. Biotechnol. Biochem. 2005 , 69 , 145 – 148 .
  • Payne , G. B. ; Deming , P. H. ; Williams , P. H. Reactions of hydrogen peroxide, VII: Alkali-catalyzed epoxidation and oxidation using a nitrile as co-reactant . J. Org. Chem. 1961 , 26 , 659 – 663 .
  • Payne , G. B. A simplified procedure for epoxidation by benzonitrile–hydrogen peroxide: Selective oxidation of 2-allylcyclohexanone . Tetrahedron 1962 , 18 , 763 – 765 .
  • Murray , R. W. ; Iyanar , K. Olefin epoxidations using the dicyclohexylcarbodiimide–H2O2 system . J. Org. Chem. 1998 , 63 , 1730 – 1731 .
  • Majetich , G. ; Hicks , R. ; Sun , G. R. ; McGill , P. Carbodiimide-promoted olefin epoxidation with aqueous hydrogen peroxide . J. Org. Chem. 1998 , 63 , 2564 – 2573 .
  • von Holleben , M. L. A. ; Livotto , P. R. ; Schuch , C. M. Experimental and theoretical study on the reactivity of the R-CN/H2O2 system in the epoxidation of unfunctionalized olefins . J. Braz. Chem. Soc. 2001 , 12 , 42 – 46 .
  • Cooper , M. S. ; Heaney , H. ; Newbold , A. J. ; Sanderson , W. R. Oxidation reactions using urea hydrogen–peroxide—A safe alternative to anhydrous hydrogen peroxide . Synlett 1990 , 533 – 535 .
  • Taliansky , S. Urea–hydrogen peroxide complex . Synlett 2005 , 1962 – 1963 .
  • Ji , L. ; Liu , J. Q. ; Qian , C. ; Chen , X. Z. Advances in the application of urea–hydrogen peroxide to oxidation reactions . Chin. J. Org. Chem. 2012 , 32 , 254 – 265 .
  • Patil , G. S. ; Nagendrappa , G. Epoxidation of cyclic vinylsilanes by urea–hydrogen peroxide complex . Synth. Commun. 2002 , 32 , 2677 – 2681 .
  • Adam , W. ; Mitchell , C. M. Methyltrioxorhenium(VII)-catalyzed epoxidation of alkenes with the urea hydrogen peroxide adduct . Angew. Chem., Int. Ed. 1996 , 35 , 533 – 535 .
  • Ankudey , E. G. ; Olivo , H. F. ; Peeples , T. L. Lipase-mediated epoxidation utilizing urea–hydrogen peroxide in ethyl acetate . Green Chem. 2006 , 8 , 923 – 926 .
  • Arias , L. A. ; Adkins , S. ; Nagel , C. J. ; Bach , R. D. Epoxidation of alkenes with trichloroacetonitrile/hydrogen peroxide in a neutral biphasic solvent system . J. Org. Chem. 1983 , 48 , 888 – 890 .
  • Braghiroli , F. L. ; Barboza , J. C. S. ; Serra , A. A. Sonochemical epoxidation of cyclohexene in R-CN/H2O2 system . Ultrason. Sonochem. 2006 , 13 , 443 – 445 .
  • Constantino , M. G. ; Lacerda , V. ; Invernize , P. R. ; da Silva , L. C. ; da Silva , G. V. J. Opening of epoxide rings catalyzed by niobium pentachloride. Synth. Commun. 2007, 37, 3529–3539.
  • Brougham , P. ; Cooper , M. S. ; Cummerson , D. A. ; Heaney , H. ; Thompson , N. Oxidation reactions using magnesium monoperphthalate—A comparison with meta-chloroperoxybenzoic acid . Synthesis 1987 , 1015 – 1017 .
  • Curci , R. ; Fiorentino , M. ; Troisi , L. ; Edwards , J. O. ; Pater , R. H. Epoxidation of alkenes by dioxirane intermediates generated in the reaction of potassium caroate with ketones . J. Org. Chem. 1980 , 45 , 4758 – 4760 .
  • Kang , B. ; Kim , M. ; Lee , J. ; Do , Y. ; Chang , S. Trimanganese complexes bearing bidentate nitrogen ligands as a highly efficient catalyst precursor in the epoxidation of alkenes . J. Org. Chem. 2006 , 71 , 6721 – 6727 .

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