The formation of dibenzodioxocin structures by oxidative coupling. A model reaction for lignin biosynthesis

DOI: 10.1016/0040-4039(95)00769-9

Source and publish data:

Tetrahedron Letters p. 4501 - 4504 (1995)

Update date:2022-07-31

Topics: Lignin Oxidative Coupling Biosynthesis

Authors:

Karhunen

Karhunen, Pirkko

Rummakko

Rummakko, Petteri

Sipila Sipila

Sipilae, Jussi

Brunow Brunow

Brunow, Goesta

Kilpelainen

Kilpelaeinen, Ilkka

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Article abstract of DOI:10.1016/0040-4039(95)00769-9

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.

Full text of DOI:10.1016/0040-4039(95)00769-9

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