Rhodium
(Chief Bee)
11-25-03 14:01
No 473067
      Allylbenzenes -> Phenylacetaldehyde(-aldoxime)
(Rated as: excellent)
    

This procedure makes allylbenzenes good phenethylamine precursors - just reduce the substituted phenylacetaldoxime to the phenetylamine using any known method.

The Oxidation of Allylbenzenes by the System RuCl3-NaIO4-PTC
Yoshifumi Yuasa; Shiroshi Shibuya; Yoko Yuasa
Synth. Commun. 33(22), 3947-3952 (2003) (../rhodium /allylbenzene2phenylacetaldehyde.html)
DOI:10.1081/SCC-120026319

Abstract
Methyleugenol 1a was oxidized to give 3,4-dimethoxyphenylacetaldehyde by the oxidative system containing the RuCl3-NaIO4-phase transfer catalyst. The yield and spectroscopic properties were obtained from the stable acetaldoxim 3a. Furthermore, this oxidation system could be applied to other arylpropenes, thus, safrole, 4-methoxyallylbenzene, allylbenzene, and the corresponding arylacetaldehyde formed.