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Synthetic Communications
An International Journal for Rapid Communication of Synthetic Organic Chemistry
Volume 31, 2001 - Issue 6
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Original Articles

NICKEL/ZINC-MEDIATED ALKYL CARBON-OXYGEN BOND CLEAVAGE OF ALKYL ARYL ETHERS

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Pages 869-875 | Received 10 Apr 2000, Published online: 09 Nov 2006

REFERENCES AND NOTES

  • Greene , T. W. and Wuts , P. G. 1991 . Protective Groups in Organic Synthesis , 2nd Ed New York : John Wiley & Sons . Chap. 3.
  • Bhatt , M. V. and Kulkarni , S. U. 1983 . Synthesis , : 249
  • Kawasaki , I. , Matsuda , K. and Kaneko , T. 1971 . Bull. Chem. Soc. Jpn. , 44 : 986
  • Benton , F. L. and Dillon , T. E. 1942 . J. Am. Chem. Soc. , 64 : 1128
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  • Brooks , P. R. , Wirtz , M. C. , Vetelino , M. G. , Rescek , D. M. , Woodworth , C. F. , Morgan , B. P. and Coe , J. W. 1999 . J. Org. Chem. , 64 : 9719 Recently, a mild and selective combined reagent (n-Bu4NI/BCl3) for the cleavage of primary alkyl aryl ethers was reported.
  • Tsuji , J. 1994 . Palladium Reagents and Catalysts 87 New York : John Wiley & Sons .
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  • Nickel(II) chloride was dried at 150°C in vacuo for 3 h and immediately used for the reaction .
  • Hauser , C. R. and Breslow , D. S. 1955 . Org. Synth., Coll. , III : 408 Zinc powder was activated as follows: Acetic acid (200 mL) was added to zinc powder (40 g) and stirred overnight. Acetic acid was removed by decantation, washed with ether three times, and dried under reduced pressure.
  • Llamas-Saiz , A. L. , Claramunt , R. M. , Cabildo , P. and Elguero , J. 1998 . J. Mol. Struct. , 440 : 193
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