The oxidation of aryl 1-methyl-1-phenylethyl sulfides promoted by the nonheme iron(IV)-oxo complexes [(N4Py)FeIVO]2+ and [(Bn-TPEN)FeIVO]2+ occurs by an electron transfer-oxygen rebound (ET-OT) mechanism leading to aryl 1-methyl-1-phenylethyl sulfoxides accompanied by products derived from Cα-S fragmentation of sulfide radical cations (2-phenyl-2-propanol and diaryl disulfides). For the first time, the rate constants for the oxygen rebound process (kOT), which are in the range of <0.8 × 104 to 3.5 × 104 s-1, were determined from the fragmentation rate constants of the radical cations (kf) and the S oxidation/fragmentation product ratios.

Electron transfer mechanism in the oxidation of Aryl 1-Methyl-1-phenylethyl sulfides promoted by nonheme Iron(IV)-oxo complexes: the rate of the oxygen rebound process / Barbieri, Alessia; Del Giacco, Tiziana; DI STEFANO, Stefano; Lanzalunga, Osvaldo; Lapi, Andrea; Mazzonna, Marco; Olivo, Giorgio. - In: JOURNAL OF ORGANIC CHEMISTRY. - ISSN 1520-6904. - STAMPA. - 81:24(2016), pp. 12382-12387. [10.1021/acs.joc.6b02434]

Electron transfer mechanism in the oxidation of Aryl 1-Methyl-1-phenylethyl sulfides promoted by nonheme Iron(IV)-oxo complexes: the rate of the oxygen rebound process

BARBIERI, ALESSIA;DI STEFANO, Stefano;LANZALUNGA, Osvaldo
;
LAPI, Andrea;MAZZONNA, MARCO;OLIVO, GIORGIO
2016

Abstract

The oxidation of aryl 1-methyl-1-phenylethyl sulfides promoted by the nonheme iron(IV)-oxo complexes [(N4Py)FeIVO]2+ and [(Bn-TPEN)FeIVO]2+ occurs by an electron transfer-oxygen rebound (ET-OT) mechanism leading to aryl 1-methyl-1-phenylethyl sulfoxides accompanied by products derived from Cα-S fragmentation of sulfide radical cations (2-phenyl-2-propanol and diaryl disulfides). For the first time, the rate constants for the oxygen rebound process (kOT), which are in the range of <0.8 × 104 to 3.5 × 104 s-1, were determined from the fragmentation rate constants of the radical cations (kf) and the S oxidation/fragmentation product ratios.
oxidation; amino acids; nonheme iron complex; hydrogen peroxide
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Electron transfer mechanism in the oxidation of Aryl 1-Methyl-1-phenylethyl sulfides promoted by nonheme Iron(IV)-oxo complexes: the rate of the oxygen rebound process / Barbieri, Alessia; Del Giacco, Tiziana; DI STEFANO, Stefano; Lanzalunga, Osvaldo; Lapi, Andrea; Mazzonna, Marco; Olivo, Giorgio. - In: JOURNAL OF ORGANIC CHEMISTRY. - ISSN 1520-6904. - STAMPA. - 81:24(2016), pp. 12382-12387. [10.1021/acs.joc.6b02434]
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Utilizza questo identificativo per citare o creare un link a questo documento: https://hdl.handle.net/11573/924299
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