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Synthetic Communications
An International Journal for Rapid Communication of Synthetic Organic Chemistry
Volume 25, 1995 - Issue 11
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Original Articles

A Convenient Synthesis Of Isopropyl Ethers from Secondary Alcohols

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Pages 1633-1639 | Received 12 Oct 1994, Published online: 23 Sep 2006

References

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  • Pine , S. H. , Zahler , R. , Evans , D. A and Grubbs , R. H. 1980 . J. Am. Chem. Soc. , 102 : 3270
  • Marra , A. , Esnault , J. , Veyrieres , A. and Sinay , P. 1992 . J. Am. Chem. Soc. , 114 : 6354
  • Petasis , N. A. and Bzowej , E. I. 1990 . J. Am. Chem. Soc. , 112 : 6392
  • Csuk , R. and Glanzer , B. I. 1991 . Tetrahedron , 47 : 1655
  • All compounds gave satisfactory TLC, HPLC, 1H NMR, 13C NMR, mass spectral, and elemental analysis data, in agreement with their assigned structures. .
  • Clark-Still , W. , Kahn , M. and Mitra , A. 1978 . J. Org. Chem. , 43 : 2923
  • Catalytic hydrogenation of the enol ethers to the isopropyl ethers was also both clean and efficient using palladium on barium sulphate 5%, palladium on charcoal 5%, palladium on charcoal 5% buffered with triethylamine, and the Lindlar catalyst. The milder catalysts are to be prefered when H2 sensitive protecting groups are present in the substrate.

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