Journal
JOURNAL OF CATALYSIS
Volume 206, Issue 2, Pages 349-357Publisher
ACADEMIC PRESS INC ELSEVIER SCIENCE
DOI: 10.1006/jcat.2001.3493
Keywords
manganese(III) porphyrins; epoxidation; oxidative dehydrogenation; alpha-pinene; 5-vinyl-2-norbornene; alpha-terpinene
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A comparative study involving four manganese(III) porphyrin catalysts combined with two different oxidants (sodium hypochlorite and potassium monopersulfate) has been performed in the epoxidation of three terpene derivatives. The catalytic oxidation of alpha-pinene produces selectively 100% of the epoxide or 65% of allylic oxidation products, only by modification of the substituents on the meso-positions of the metalloporphyrin catalyst. The catalytic oxidation of the 5-vinyl-2-norbornene is regio- and stereoselective, producing only the exo-2,3-epoxy-5-vinylnorbornane. With alpha-terpinene, a conjugated di-olefin, an oxidative dehydrogenation reaction was surprisingly observed, producing p-cymene as a major compound. (C) 2002 Elsevier Science (USA).
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