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Synthetic Communications
An International Journal for Rapid Communication of Synthetic Organic Chemistry
Volume 10, 1980 - Issue 12
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Original Articles

A New Protecting Group for Phenols: Phenylthiomethyl (PTM) Ethers

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Pages 911-914 | Published online: 05 Dec 2006

References

  • Virginia Polytechnic Institute and State University
  • Corey , E. J. and Bock , M. G. 1975 . Tetrahedron Lett. , : 3269
  • Pojer , P. M. and Angyal , S. J. 1976 . Tetrahedron Lett. , : 3067
  • Yamada , K. , Kato , K. , Nagase , H. and Hirata , Y. 1976 . Tetrahedron Lett. , : 65
  • Holton , R. A. and Davis , R. G. 1977 . Tetrahedron Lett. , : 533
  • Trost , B. M. and Kunz , R. A. 1974 . J. Org. Chem. , 39 : 2649 Conveniently prepared by the method of
  • All new compounds were characterized by correct C, H combustion analyses and spectral data in accord with assigned structures
  • Yields refer to spectrally and chromatographically homogeneous isolated material
  • All attempts to prepare PTM ethers of alcohols (p,-aethyl benzyl alcohol, menthol) were unsuccessful due to the formation of numerous side products. Presumably, these difficulties may be attributed to the increased acidity of iodomethyl phenyl sulfice (relative to chloromethyl methyl sulfide) and the increased basicity of the sodium alkoxides
  • Kohler , E. P. and Chadwell , H. M. 1932 . Org. Syn. Coll. , Vol. 1 : 78

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