One Electron Oxidation of α-Alkylbenzyl Alcohols Induced by Potassium 12-Tungstocobalt(III)ate − Comparison with the Oxidation Promoted by Microsomal Cytochrome P450
✍ Scribed by Enrico Baciocchi; Sandro Belvedere; Massimo Bietti; Osvaldo Lanzalunga
- Publisher
- John Wiley and Sons
- Year
- 1998
- Tongue
- English
- Weight
- 361 KB
- Volume
- 1998
- Category
- Article
- ISSN
- 1434-193X
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✦ Synopsis
The chemical and microsomal oxidations of a number of 4-tion process. In contrast, the microsomal oxidation of the two substrates 3 and 4 led in both cases to the exclusive formation methoxy substituted α-alkylbenzyl alcohols 4-MeOPh-CH(R)OH (E ox = 1.6Ϫ1.7 V vs SCE) were investigated. Using of the corresponding ketone. Thus, an electron transfer mechanism appears unlikely for the microsomal oxidation of potassium 12-tungstocobalt(III)ate, a bona fide one electron oxidant, competition between C α ϪH and C α ϪC β bond cleav-α-alkylbenzyl alcohols, even though the oxidation potential of these species is lower than or comparable to that of the age in the intermediate radical cation was observed when the side-chain alkyl group R was Et (2) and iPr (3). With R = active oxidant in the enzyme. A hydrogen atom transfer mechanism is more in line with these results. Me (1), only CϪH bond cleavage took place, whereas with R = tBu (4) CϪC bond cleavage was the exclusive fragmenta-