- Structures of oxidation products of 4,6-di-tert-butylpyrogallol
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Oxidation of 4,6-di-tert-butylpyrogallol gave two dimeric products instead of the expected 4,6-di-tert-butyl-3-hydroxy-1,2-benzoquinone (2). It was established by X-ray diffraction analysis that the first product has the structure of tetra-tert-butyl-6,10
- Shif,Lyubchenko,Borbulevych,Shishkin,Lyssenko,Olekhmovich
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p. 139 - 146
(2007/10/03)
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- Mechanism of C-C Cleavage of Cyclic 1,2-Diketones with Alkaline Hydrogen Peroxide. The Acyclic Mechanism and Its Application to the Basic Autooxidation of Pyrogallol
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The reaction of 3,5-di-tert-butyl-o-benzoquinone (3) with alkaline hydrogen peroxide was found to give a considerable amount of methyl ester 5 when H2O2 was added dropwise.In contrast, the corresponding diacids were not obtained from o-benzoquinone or 1,2-naphthoquinone on reaction with alkaline H2O2.An 18O-tracer study of the reaction of 3 and 9,10-phenanthrenequinone indicated that the C-C cleavage reaction proceeds via the acyclic Baeyer-Villiger type mechanism and clearly eliminated possible dioxetane or epoxide mechanisms.A similar study of the base-catalyzed autooxidation of 4,6-di-ter-butylpyrogallol revealed that the C-C bond is cleaved in a similar way by hydrogen peroxide formed from O2 and the polyphenol.
- Sawaki, Yasuhiko,Foote, Christopher S.
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p. 5035 - 5040
(2007/10/02)
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