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Synthetic Communications
An International Journal for Rapid Communication of Synthetic Organic Chemistry
Volume 32, 2002 - Issue 8
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Original Articles

RUTHENIUM-CATALYZED FACILE AEROBIC OXIDATION OF α-HYDROXYCARBONYLS TO 1,2-DICARBONYL COMPOUNDS

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Pages 1279-1284 | Received 26 Mar 2001, Published online: 16 Aug 2006

REFERENCES

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  • Weiss , M. and Appel , M. 1948 . J. Am. Chem. Soc. , 70 : 3666
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  • Tymonko , S.A. , Nattier , B.A. and Mohan , R.S. 1999 . Tetrahedron Lett. , 40 : 7657
  • Kirihara , M. , Ochiai , Y. , Takizawa , S. , Takahata , H. and Nemoto , H. 1999 . Chem. Commun. , : 1387
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  • Furniss , B.S. , Hannaford , A.J. , Smith , P.W.G. and Tatchell , A.S. 1989 . Vogel's Textbook of Practical Organic Chemistry 1045 Essex, , UK : Longman Scientific & Technical . Starting materials of α-hydroxycarbonyl compounds were prepared according to the reported procedure
  • Although complete conversion was also observed within 4 h for this substrate, the moderate isolated yield for the product was partly due to competitive decarbonylation of the substrate under the reaction conditions.
  • The aerobic oxidation did not proceed at any significant rates in the presence of secondary amines such as piperidine or pyrroridine instead of tertiary amines under otherwise identical conditions.
  • Kirihara , M. , Takizawa , S. and Momose , T. 1998 . J. Chem. Soc., Perkin Trans. 1 , : 7 For a previous example of the metal-catalyzed oxidative cleavage of α-hydroxyketones

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