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Synthetic Communications
An International Journal for Rapid Communication of Synthetic Organic Chemistry
Volume 20, 1990 - Issue 20
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Original Articles

Minimizing Geometric Isomerization During Oxidation of Allylic Alcohols to Aldehydes

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Pages 3125-3130 | Received 13 Aug 1990, Published online: 24 Oct 2006

References

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  • Barton , D. H.R. , Kitchin , J. P. and Motherwell , W. B. 1978 . J. Chem. Soc., Chem. Commun. , : 1099
  • Santaniello , E. and Ferraboshi , P. 1980 . Synth. Commun. , 10 : 75
  • Matsumoto , M. and Watanabe , N. 1984 . J. Org. Chem. , 49 : 3436
  • Fatiadi , A. J. 1976 . Synthesis , : 65 and 133 For a recent review, see:
  • Synthesis and biological study of cyclopropyl epoxysqualenes will be published in another place soon
  • De Wolfe , R. H. and Young , W. G. 1950 . Chem. Rev. , 56 : 753
  • Allinger , N. L. , Cava , M. P. , de Jongh , O. C. , Johnson , C. R. , Lebel , N. A. and Stevens , C. L. 1972 . Organic Chemistry , 509 Worth Publishers, Inc. .
  • Prepared by hydrogenation (H2/Pd-CaSO4) of phenylpropargyl alcohol, which was synthesized from phenylacetylene magnesium bromide and paraformaldehyde. Z:E ratio was more than 99:1 either by capillary GC or by proton NMR analysis
  • Intermediate in the synthesis of cyclopropyl epoxysqualene analogs. See ref. 6
  • All compounds have satisfactory spectroscopic data (FT-IR, NMR, and/or GC/MS) compared with reported data, if known, or with assigned structure, if new

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