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Type: Artigo de periódico
Title: Transition-metal catalyzed autoxidation of cis- and trans-pinane to a mixture of diastereoisomeric pinanols
Author: Sercheli, R
Ferreira, ALB
Baptistella, LHB
Schuchardt, U
Abstract: Autoxidations of the pinanes, obtained after hydrogenation of naturally occurring Pinus elliottii oil, were performed with or Without solvent, using the catalytic system Co(OAc)(2)/Mn(OAc)(2)/NH4Br in a 9:1:5 molar ratio, and dioxygen as the oxidant. The best selectivity for the pinanols was 71% (cis:trans ratio, 3:1) with 17% conversion. Autoxidations were also carried out in the absence of catalyst. The hydroperoxides formed with 17% conversion were decomposed with Na2SO3 and PPh3, resulting in 62% pinanols (cis:trans ratio, 5:1). The pyrolysis of the pinanols at 600 degrees C and a contact time of 1.15 x 10(-2) s/mol yielded 54% of linalool. The side products were mainly due to an 'ene' reaction, giving diastereoisomeric 1,2-dimethyl-3-isopropenylcyclopentanols.
Subject: catalytic oxidation
Editor: Amer Chemical Soc
Rights: fechado
Identifier DOI: 10.1021/jf960472q
Date Issue: 1997
Appears in Collections:Artigos e Materiais de Revistas Científicas - Unicamp

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