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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 ?p-constants.The rho-values are -2.60 for chromic acid and 0.72 for TBHP/VO(acac)2.A poor correlation with rho =-0.17 (r = 0.756) was obtained for TBHP/Rh(PPh3)3Cl.It is included that the Rh-catalyzed reaction does not consist in electrophilic oxygen transfer to the anthracene.
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Reference：
Metal catalyst and ligand design,
Ligand Template Strategies for Catalyst Encapsulation – NCBI