Oxidation of Benzoins to Benzils with Chromium Trioxide Under Viscous Conditions

REFERENCES

• Fieser , L. F. ; Fieser , M. Reagents for Organic Synthesis ; John Wiley & Sons : New York , 1967 ; vol. 1 , pp. 1059 – 1064 , and subsequent volumes in the series .
   Google Scholar
• Freeman , F. In Organic Synthesis by Oxidation with Metal Compounds ; W. J. Mijs , C. R. H. I. de Jonge (Eds.); Plenum Press : New York , 1986 ; pp. 68 – 81 .
   Google Scholar
• Ley , S. V. ; Madin , A. In Comprehensive Organic Synthesis ; B. Trost , M. I. Fleming (Eds.); Pergamon Press : London , 1991 ; vol. 7 , pp. 251 – 289 .
   Google Scholar
• Harding , K. E. ; May , L. M. ; Dick , K. F. Selective oxidation of allylic alcohols with chromic acid . J. Org. Chem. 1975 , 40 , 1664 – 1665 , and references cited therein .
   Web of Science ®Google Scholar
• Rao , Y. S. ; Filler , R. Novel method for the oxidation of primary and secondary alcohols to carbonyl compounds . J. Org. Chem. 1974 , 39 , 3304 – 3305 .
   Web of Science ®Google Scholar
• Morrison , H. ; Danishefsky , S. ; Yates , P. Preparation of α-diazo ketones . J. Org. Chem. 1961 , 26 , 2617 – 2618 .
   Web of Science ®Google Scholar
• Matsushita Electric Industrial Co. Ltd. Photohardenable resin compositions . Jpn. Kokai Tokkyo Koho 1981 , 8198203 ; Chem. Abstr. 1981, 95, 188163u .
   Google Scholar
• Vollhardt , K. P. C. ; Schore , N. E. Organic Chemistry, , 2nd ed. ; Freeman : New York , 1994 ; pp. 924 – 929 .
   Google Scholar
• Mitra , A. K. ; De , A. ; Karchaudhuri , N. Microwave-assisted syntheses of 1,2-diketones . J. Chem. Res., Synop. 1999 , 246 – 247 .
   Google Scholar
• Vogel , A. Textbook of Practical Organic Chemistry including Qualitative Organic Analysis, , 4th. Ed. ; Longman : New York , 1978 ; p. 883 .
   Google Scholar
• Joul , J. A. ; Mills , K. ; Smith , G. F. Heterocyclic Chemistry, , 3rd ed. ; Chapman & Hall : London , 1995 .
   Google Scholar
• Filippo , J. S. ; Chern , C.-I. Chemisorbed chromyl chloride as a selective oxidant . J. Org. Chem. 1977 , 42 , 2182 – 2183 .
   Web of Science ®Google Scholar
• Tamami , B. ; Goudarzian , N. Quinaldinium and poly(2-vinyl-quinolinium) dichromates as new monomeric and polymeric oxidizing reagents . J. Sci. I. R. Iran 1990 , 1 , 372 – 376 .
   Google Scholar
• Zhang , G. S. ; Shi , Q. Z. ; Chen , M. F. ; Cai , K. Ammonium chlorochromate adsorbed on alumina: A new reagent for oxidation of alcohols and benzoins to the corresponding carbonyl compounds . Synth. Commun. 1997 , 27 , 953 – 956 .
   Web of Science ®Google Scholar
• Zhang , G. S. ; Shi , Q. Z. ; Chen , M. F. ; Cai , K. Ammonium chlorochromate adsorbed on silica gel: A new reagent for oxidation of alcohols and benzoins to the corresponding carbonyl compounds . Synth. Commun. 1997 , 27 , 3691 – 3696 .
   Web of Science ®Google Scholar
• Heravi , M. M. ; Kiakajoori , R. ; Hayder , K. T. Ammonium chlorochromate adsorbed on montmorillonite K-10: Selective oxidation of alcohols under solvent-free conditions. J. Chem. Res., Synop. 1998, 656–657.
   Google Scholar
• Heravi , M. M. ; Kiakajoori , R. ; Mojahedi , M. M. Oxidation of alcohols by silica gel–supported ammonium chlorochromate in solventless system . Indian J. Chem. 2001 , 40B , 219 – 330 .
   Google Scholar
• Li , J.-T. ; Liu , X.-R. ; Wang , W.-F. An efficient oxidation of benzoins to benzils by ACC/silica gel under ultrasound irradiation . Ultrasonics Sonochem. 2009 , 16 , 331 – 333 .
   PubMed Web of Science ®Google Scholar
• Varma , R. S. ; Saini , R. K. Wet alumina–supported chromium(VI) oxide: Selective oxidation of alcohols in solventless system . Tetrahedron Lett. 1998 , 39 , 1481 – 1482 .
   Web of Science ®Google Scholar
• Lou , J. D. ; Li , L. ; Vatanian , N. ; Lu , X. L. ; Yu , X. Selective oxidation of α-hydroxy ketones to α-diketones with chromium trioxide supported on kieselguhr reagent . Synth. React. Inorg. Met.-Org. Chem. 2008 , 38 ( 4 ), 373 – 375 .
   Google Scholar
• Lou , J. D. ; Zhang , C. ; Wang , G. Q. Oxidation of benzoins to benzils with chromium trioxide supported on kieselguhr under viscous conditions . Synth. React. Inorg. Met.-Org. Chem. 2009 , 39 ( 1 ), 6 – 8 .
   Web of Science ®Google Scholar
• Lou , J. D. ; Vatanian , N. ; Zhang , C. ; Wang , G. Q. Oxidation of benzoins with chromium trioxide in dimethyl sulfoxide . Synth. React. Inorg. Met.-Org. Chem. 2009 , 39 ( 3 ), 121 – 123 .
   Web of Science ®Google Scholar
• Zhang , G.-S. ; Shi , Q.-Z. ; Cai , K. Trimethylammonium chlorochromate adsorbed on alumina as oxidant for alcohols and benzoins . Youji Huaxue 1998 , 18 , 263 – 267 .
   Google Scholar
• Ali , M. H. ; Wiggin , C. J. Silica gel–supported Jones reagent (SJR): A simple, versatile, and efficient reagent for oxidation of alcohols in nonaqueous media . Synth. Commun. 2001 , 31 , 3383 – 3393 .
   Web of Science ®Google Scholar
• Mohammadpoor-Baltork , I. ; Sadeghi , M. M. ; Adibi , A.-H. Efficient, solvent-free oxidation of organic compounds with potassium dichromate in the presence of Lewis acids . Molecules 2001 , 6 , 900 – 908 .
   Web of Science ®Google Scholar
• Degirmenbasi , N. ; Ozgun , B. Quinoxalinium bromochromate—A new and efficient reagent for oxidation of alcohols and bromination of aromatic compounds . G. U. J. Sci. 2006 , 19 , 9 – 13 .
   Google Scholar
• Cainelli , G. ; Cardillo , G. Chromium Oxidation in Organic Chemistry ; Springer : Berlin , 1984 .
   Google Scholar
• Aydini , F. ; Turunc , E. The use of pyridinium fluorochromate (PFC) supported on TriSyl silica gel for oxidation reactions . J. Serb. Chem. Soc. 2007 , 72 , 129 – 132 .
   Web of Science ®Google Scholar
• Sahu , A. ; Rawal , M. K. ; Sharma , V. K. ; Parashar , B. Microwave-assisted oxidation of benzoin on alumina using chromium-based oxidants . Internat. J. ChemTech Res. 2009 , 1 , 1087 – 1089 .
   Google Scholar
• Lou , J. D. ; Xu , Z. N. Selective oxidation of primary alcohols with chromium trioxide under solvent-free conditions . Tetrahedron Lett. 2002 , 43 , 6095 – 6097 .
   Web of Science ®Google Scholar
• Lou , J. D. ; Lu , X. L. ; Marrogi , A. J. ; Li , F. ; Gao , C. L. ; Yu , X. A first example for a reaction under viscous conditions: Oxidation of solid benzoins with manganese dioxide . Monatsh. Chem. 2008 , 139 , 609 – 611 .
   Web of Science ®Google Scholar
• Khandekar , A. C. ; Paul , A. M. ; Khadilkar , B. M. Silica-supported manganese dioxide: An efficient reagent for oxidation of benzoins . Synth. Commun. 2002 , 32 ( 19 ), 2931 – 2936 .
   Web of Science ®Google Scholar