Tetrahedron Letters p. 4501 - 4504 (1995)
Update date:2022-07-31
Topics: Lignin Oxidative Coupling Biosynthesis dibenzodioxocin
Karhunen
Karhunen, Pirkko
Rummakko
Rummakko, Petteri
Sipila
Sipilae, Jussi
Brunow
Brunow, Goesta
Kilpelainen
Kilpelaeinen, Ilkka
Oxidation of o,o'-dihydroxybiphenyl compounds together with coniferyl alcohol yields substituted 6,7-dihydro-dibenzo-(e,g)(1,4)-dioxocins, that represent a novel type of linkage in softwood lignins. The mechanism of formation of the 8-membered ring involves intramolecular nucleophilic addition to an intermediate quinone methide structure.
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(2021)