Die Bildung von Hydroxyaryl‐chinonen durch Addition von Phenolen an Chinone

Exhaustive laccase-catalysed oxidation of a lignin model compound (vanillyl glycol) produces methanol and polymeric quinoid products

“…Quinone structures like oquinones of type (III) (Scheme 1) are known to be reactive and are probably involved in the transformation of the dimers to polymeric material (Scheme 1; cf. Adler & Berggren, 1960;Flaig et al, 1963;Musso et al, 1964).…”

Oxidative Coupling of Phenols and Phenol Ethers

“…39 The oxidation of a similar chiral reactant (20) has been examined from the stereochemical viewpoint. 41 In this context it is of interest that a compound obtained (74%) on ferricyanide oxidation of MeO HO (20) (21) the 2,2'-dihydroxybiphenyl (25) proved to be the oxepinobenzofuran (26)42 rather than the benzoxete (27) as originally formulated. However, on electrooxidation at a graphite anode only one stereomer was formed (69%), the rotamer shown (21) 2-Naphthol can successfully be dimerized oxidatively, selectively through the o-site to give (22) using copper(II)-amine complexes (70%)39 or manganese(III) acetylacetonate (69%),32 and 0-0 coupling is the major pathway (90%) on ferricyanide oxidation of the trisubstituted phenol (23) to the orthodiphenoquinone (24).…”

Soil Components

“…Based on investigations of the addition of amino compounds to phloroglucinol [5] in a neutral oxidizing medium STEIN and TENDELOO [1956a, b; concluded that the first reaction step is the formation of a radical. The autoxidation of orcinol [12] (HENRICH, SCHMIDT, and ROSSTEUTSCHER [1915]) leads, in aqueous solution, to a mixture of quinones [13,14] that have been isolated by Musso [1958] (Figure 36a). Orcinol [12] and resorcinol derivatives, which are substituted in 2-and in 2,4positions with methyl groups, react in aqueous alkaline solution with hydroxy-p-benzoquinone [15] or with methyl-substituted derivatives to form the corresponding dihydroxyarylhydroxyp-benzoquinone [16] (Musso, GIZYCKI, ZAHORSKY, and BORMANN [1964]).…”

“…Monophenols substituted with tert. Musso [1963] summarized the oxidation reactions of phenols under highly variable conditions, many of which could not be involved in the formation of humic substances. Musso [1963] summarized the oxidation reactions of phenols under highly variable conditions, many of which could not be involved in the formation of humic substances.…”

“…In a summary of the oxidation of phenols Musso [1963] reported also that diphenylethers are not formed in the presence of phenol-oxidizing enzymes (see TODD [1962], LINDGREEN [l960a, b]). In a summary of the oxidation of phenols Musso [1963] reported also that diphenylethers are not formed in the presence of phenol-oxidizing enzymes (see TODD [1962], LINDGREEN [l960a, b]).…”