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Synthetic Communications
An International Journal for Rapid Communication of Synthetic Organic Chemistry
Volume 24, 1994 - Issue 8
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Original Articles

Cleavage or Acetyl-de-alkylation of 4-Methoxybenzyl (MPM) Ethers Using Acetic Acid

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Pages 1151-1155 | Received 31 Aug 1993, Published online: 23 Sep 2006

References

  • Nakajima , N. , Abe , R. and Yonemitsu , O. 1988 . Chem. Pharm. Bull. , 36 : 4244
  • Greene , T. W. and Wuts , P. G. M. 1991 . Protective Groups in Organic Synthesis , pp. 53 – 56 . New York : Wiley . 2nd ed.
  • Horita , K. , Yoshioka , T. , Tanaka , T. , Oikawa , Y. and Yonemitsu , O. 1986 . Tetrahedron , 42 : 3021 and references cited therein
  • Hodgetts , K. J. and Wallace , T. W. unpublished observations
  • An aryl MPM ether has been cleaved using stronger (trifluoroacetic) acid
  • White , J. D. and Amedio , J. C. 1989 . J. Org. Chem. , 54 : 736
  • Hébert , N. , Beck , A. , Lennox , R. B. and Just , G. 1992 . J. Org. Chem. , 57 : 1777 MPM ethers can also be cleaved with dimethylboron bromide
  • Ganem , B. and Small , V. R. 1974 . J. Org. Chem. , 39 : 3728 Acetyl-de-alkylation of ethers has also been effected using acetic anhydride/FeCl3
  • Oriyama , T. , Kimura , M. , Oda , M. and Koga , G. 1993 . Synlett , : 437 and acetyl bromide/SnBr2
  • Kano , K. and Anselme , J.-P. 1992 . Tetrahedron , 48 : 10075 The acetylation of benzyl alcohol under similar conditions (HOAc, reflux, 24 h) has been described
  • Saengchantara , S. T. and Wallace , T. W. 1990 . Tetrahedron , 46 : 6553
  • Belli , A. , Giordano , C. and Citterio , A. 1980 . Synthesis , 477
  • Lundquist , K. and Olsson , T. 1977 . Acta Chem. Scand. (B) , 31 : 788
  • Nagao , Y. , Miyusaka , T. and Hagiwara , Y. 1984 . J. Chem. Soc., Perkin Trans. I , 183
  • Taylor , R. , Smith , G. G. and Wetzel , W. H. 1962 . J. Am. Chem. Soc. , 84 : 4817
  • Horita , K. , Nagato , S. , Oikawa , Y. and Yonemitsu , O. 1989 . Chem. Pharm. Bull. , 37 : 1705

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