Preparation and behavior of simple quinone metnides

Filar, L. J.; Winstein, S.

doi:10.1016/s0040-4039(01)82682-4

Cited by 42 publications

(50 citation statements)

References 12 publications

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“…as obtained by chemical synthesis or flash photolysis of the corresponding phenols (22)(23)(24)(25)(26). However, spectra of the p-quinone methides of vanillyl alcohol and 4-(methoxymethyl)phenol have never been described.…”

Section: Discussionmentioning

confidence: 99%

Catalytic Mechanism of the Oxidative Demethylation of 4-(Methoxymethyl)phenol by Vanillyl-Alcohol Oxidase

Fraaije

Berkel

1997

Journal of Biological Chemistry

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The catalytic mechanism for the oxidative demethylation of 4-(methoxymethyl)phenol by the covalent flavoprotein vanillyl-alcohol oxidase was studied. ). The kinetic data for the oxidative demethylation of 4-(methoxymethyl)phenol are in accordance with a ternary complex mechanism in which the reduction rate is rate-limiting. It is proposed that, upon reduction, a binary complex is produced composed of the p-quinone methide of 4-(methoxymethyl)phenol and reduced enzyme.

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Section: Discussionmentioning

confidence: 99%

Catalytic Mechanism of the Oxidative Demethylation of 4-(Methoxymethyl)phenol by Vanillyl-Alcohol Oxidase

Fraaije

Berkel

1997

Journal of Biological Chemistry

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“…This quinone methide was generated in alkaline aqueous solution from chloride and acetate precursors H-38a-Cl and H-38a-OAc . 68 Stable quinone methides such as 38b-e (Scheme 19) were generated from chloride precursors H-38-Cl . 69,70 …”

Section: Generation Of Quinone Methides By Heterolytic Bond Cleavagementioning

confidence: 99%

The generation and reactions of quinone methides

Toteva

Richard

2011

Advances in Physical Organic Chemistry

132

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“…3d-f). This kind of absorption could be due to an extended conjugation of dimerization products involving the side-chain, possible when neutral phenoxyl radicals are initially formed [37][38][39], as shown in Scheme 2. Formation of dimerization products is further supported by HPLC-MS data, evidencing in all cases the presence of the corresponding molecular ione [Dim-H] − , respectively, m/z 357 for CA, m/z 325 for CUA, m/z 385 for FA and m/z 445 for SA, as shown in Fig.…”

Section: Chemical Oxidationmentioning

confidence: 99%