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Synthesis 1997; 1997(2): 153-155
DOI: 10.1055/s-1997-1165
short paper
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Oxidation of β,γ-Unsaturated Ketones with Molecular Oxygen Catalyzed by Metal Phthalocyanines and Porphyrins: A Practical Synthesis of Oxophorone

Nobuhiko Ito1 , Takeaki Etoh2 , Hisahiro Hagiwara3 , Michiharu Kato4
  • 1Research and Development Laboratories, Soda Aromatic Co., Ltd., 1573-4, Funakata, Noda, Chiba 270-02, Japan, Fax +81(471)29 8581
  • 2Research and Development Laboratories, Soda Aromatic Co., Ltd., 1573-4, Funakata, Noda, Chiba 270-02, Japan
  • 3Graduate School of Science and Technology, Niigata University, 8050, 2 Nocho, Ikarashi, Niigata 950-21, Japan
  • 4Institute for Chemical Reaction Science, Tohoku University, Katahira, Aoba-ku, Sendai 980-77, Japan
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Publication History

Publication Date:
31 December 2000 (online)

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Oxidation of 3,5,5-trimethylcyclohex-3-en-1-one (1) with molecular oxygen catalyzed by metal phthalocyanines (Pc) and 5,10,15,20-tetraphenylporphyrins (TPP) including Mn(II), Mn(III), Fe(II), Fe(III), Co(II), Cu(II), and Ru(II) to 3,5,5-trimethylcyclohex-2-ene-1,4-dione (2) was studied. TPPMn(III)Cl showed an excellent catalytic activity, affording 2 in 93% yield and 1200 turnover number.

oxidation with molecular oxygen - β,γ-unsaturated ketones - transition metal phthalocyanine - transition metal porphyrin - oxophorone

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