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Rh-Catalyzed Oxidation of Anthracenes with tert-Butyl Hydroperoxide. Kinetic Aspects (1985)

Müller, Paul ; Bobillier, Christiane

New York, NY : Wiley-Blackwell

Helvetica Chimica Acta 68 (1985), S. 450-455

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ISSN: 0018-019X

Keywords: Chemistry ; Organic Chemistry

Source: Wiley InterScience Backfile Collection 1832-2000

Topics: Chemistry and Pharmacology

Notes: The polar effects of substituents on reactivity in oxidation of 2-substituted anthracenes with tert-butyl hydroperoxide (TBHP)/Rh(PPh3)3Cl have been investigated and compared with those obtained with TBHP/VO(acac)2 and chromic acid. The anthracene reactivities obtained from competition experiments are correlated with Hammett's σp-constants. The P-values are -2.60 for chromic acid and 0.72 for TBHP/VO(acac)2. A poor correlation with p = -0.17 (r = 0.756) was obtained for TBHP/Rh (PPh3)3Cl. It is concluded that the Rh-catalyzed reaction does not consist in electrophilic oxygen transfer to the anthracene.

Additional Material: 1 Ill.

Type of Medium: Electronic Resource

URL: http://dx.doi.org/10.1002/hlca.19850680218

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