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Synthetic Communications
An International Journal for Rapid Communication of Synthetic Organic Chemistry
Volume 25, 1995 - Issue 4
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Original Articles

Oxidation of Certain 4-Substituted Phenethyl Alcohols with Collins Reagent: On the Mechanism of a Carbon-Carbon Bond Cleavage

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Pages 533-537 | Received 04 Aug 1994, Published online: 23 Sep 2006

References

  • Collins , J. C. , Hess , W. W. and Frank , F. J. 1968 . Tetrahedron Lett. , : 3363
  • Ratcliffe , R. and Rodehorst , R. 1970 . J. Org. Chem. , 35 : 4000 – 4002 .
  • The isolated product (by silica gel chromatography) was characterized by NMR and MS spectrometry and the data were found to be identical with that from an authentic sample: 1H-NMR (CDCl3) δ 10.17 (s, 1 H), 8.41 (d, 2 H, J = 8.7 Hz), 8.09 (d, 2 H, J = 8.7 Hz); EIMS m/z (relative intensity) 151 (M+, 100), 150 (M+ - H, 87), 105 (M+ - NO2, 23).
  • These two compounds (2a and 2b) were previously synthesized by oxidation of the corresponding styrenes, using lead tetraacetatea and thallium (III) nitrate,b respectively
  • Lethbridge , A. , Norman , R. O. C. and Thomas , C. B. 1973 . J. Chem. Soc. Perkin I , : 35 – 38 .
  • McKillop , A. and Hunt , J. D. 1970 . Tetrahedron Lett. , 60 : 5275 – 5280 .
  • Bijoy , P. and Rao , G. S. R. S. 1993 . Synth. Commun. , 23 : 2701 – 2708 .

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