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Evidence of a SN2-Set Continuum in the Oxidation of Organic Sulfides By Peroxovanadium Complexes

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The oxidation of di-n-butyl sulfide and phenylmethyl sulfide by two vanadium (V) peroxocomplexes, e.g. VO(O2)OCH3, 1, and VO(O2)(PIC)(H2O)2, 2, in methanol, was investigated. The kinetic analysis of the reactions revealed significant mechanistic differences between the two peroxometal oxidants. In particular, 1 behaves as an electrophilic oxidant so that the transition state of sulfide oxidations by 1 may be described as a SN2 displacement on the peroxide oxygen whereas 2 acts as a radical oxidant in a process which has a substantial SET character. The role of the picolinato ligand in determining the reactivity of 2 is discussed in terms of a decrease of the electrophilicity of the peroxide oxygen compared with 1 and of a stabilization of the radical metal species.

Affiliations: 1: Centro CNR di Studio sui Meccanismi di Reazioni Organiche Dipartimento di Chimica Organica Università di Padova Via Marzolo 1, 35131 Padova, Italy


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