- Investigate cleavage of β-O-4 linkage in lignin model compounds by aerobic oxidation of Cα and Cγ hydroxyl groups
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The selective cleavage of common linkages in lignin polymers is a promising approach to generate valuable aromatic hydrocarbons. Herein, we found that on oxidation of Cα and Cγ hydroxyl groups in β-O-4 lignin model compounds with TEMPO catalyst resulted in the formation of 1,3-dicarbonyl TEMPO adduct. These oxidized products readily underwent fragmentation at Cα-Cβ bond in the presence of a catalytic amount of acid to generate corresponding carboxylic acid and phenol monomers.
- Patil, Nikhil D.,Yan, Ning
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supporting information
p. 3024 - 3028
(2016/07/06)
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- Selective cleavage of the Cα-Cβ linkage in lignin model compounds via Baeyer-Villiger oxidation
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Lignin is an amorphous aromatic polymer derived from plants and is a potential source of fuels and bulk chemicals. Herein, we present a survey of reagents for selective stepwise oxidation of lignin model compounds. Specifically, we have targeted the oxidative cleavage of Cα-Cβ bonds as a means to depolymerize lignin and obtain useful aromatic compounds. In this work, we prepared several lignin model compounds that possess structures, characteristic reactivity, and linkages closely related to the parent lignin polymer. We observed that selective oxidation of benzylic hydroxyl groups, followed by Baeyer-Villiger oxidation of the resulting ketones, successfully cleaves the Cα-Cβ linkage in these model compounds. This journal is
- Patil, Nikhil D.,Yao, Soledad G.,Meier, Mark S.,Mobley, Justin K.,Crocker, Mark
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p. 3243 - 3254
(2015/03/18)
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- Synthesis and N.m.r. Spectra of 2,6- and 2,4-Diaryl-3,7-dioxabicyclooctanes
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A series of isomeric 2,6- and 2,4-diaryl-3,7-dioxabicyclooctanes have been prepared via the corresponding threo, and erythro-dioxo-diesters.Comparison of their 1H and 13C n.m.r. spectra reveals small differences in chemical shifts and coupling constants which could be diagnostic in assigning structures to such compounds.The structure of 4-hydroxysesamin has been confirmed by direct correlation with sesamin.
- Pelter, Andrew,Ward, Robert S.,Watson, Derrick J.,Jack, Ibiba R.
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p. 183 - 190
(2007/10/02)
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