Revisiting the mechanism of
 β
 -
 O
 -4 bond cleavage during acidolysis of lignin. Part 8: Comparison between phenolic and non-phenolic C
 6
 -C
 2
 -type model compounds

Ye, Qiaoqiao; Yokoyama, Tomoya

doi:10.1080/02773813.2021.1986072

Cited by 4 publications

(1 citation statement)

References 16 publications

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“…S6-S8 †). The differences between the phenolic and non-phenolic β-O-4 linkage during acidolysis mainly lie in the conversion rate (the conversion rate of phenolic β-O-4 is 2-11 times faster than the non-phenolic counterpart depending on the acids applied), which has been studied in detail by Yokoyama et al, 46 and Beckham et al 39 DFT calculations suggested that the rate increase is due to the stabilization of the carbocation intermediate by delocalization of benzylic carbocation in the phenolic β-O-4. 39 In this study, the non-phenolic β-O-4 model compound was used for further investigations due to its dominant existence in lignin.…”

Section: C3 β-O-4 Model Acidolysis With Different Metal Triflatesmentioning

confidence: 99%

Chemicals from lignin by diol-stabilized acidolysis: reaction pathways and kinetics

et al. 2022

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Section: C3 β-O-4 Model Acidolysis With Different Metal Triflatesmentioning

confidence: 99%

Chemicals from lignin by diol-stabilized acidolysis: reaction pathways and kinetics

et al. 2022

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Revisiting the mechanism of β - O -4 bond cleavage during acidolysis of lignin. Part 9: Comprehensive results for guaiacyl-type compounds and the difference in participation mode of bromide and chloride anions between C ₆ -C ₃ -type and C ₆ -C ₂ -type compounds

Ye,

Katsumata,

Komatsu

et al. 2024

Journal of Wood Chemistry and Technology

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Revisiting the mechanism of β-O-4 bond cleavage during acidolysis of lignin part 10: reactions of C6–C2-type non-phenolic syringyl model compounds and comparison of the reactions with those of the guaiacyl analogues

Mizutani,

Katsumata,

Komatsu

et al. 2024

J Wood Sci

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A C6–C2-type non-phenolic syringyl lignin model compound (I, 2-(2-methoxyphenoxy)-1-(3,4,5-trimethoxyphenyl)ethanol) as well as its derivatives was acidolyzed in aqueous 82vol% 1,4-dioxane containing 0.2 mol/L HBr, HCl, or H2SO4 at 85ºC. The results were compared with those on the guaiacyl analogues (V as well as its derivatives) obtained in our previous reports. The acidolysis of compound I was slower than that of compound V, which is in accordance with our previous result on the formation rates of the benzyl cation intermediates (BC) from a syringyl compound and its guaiacyl analogue. The enol ether-type compound was primarily produced in the acidolysis of compound I, similar to that of compound V. The acidolysis using HBr or HCl was faster than that using H2SO4, indicating the participation of Br¯ or Cl¯, respectively, in the acidolysis. It was suggested that Br¯ (as well as Cl¯) adds to the cation center of the BC to afford the adduct in the acidolysis of compound I, similar to that of compound V, and hence, this adduct formation is a major bypass of the common route. The bypass activity in the acidolysis of compound I was about half in that of compound V.

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Revisiting the mechanism of β - O -4 bond cleavage during acidolysis of lignin. Part 8: Comparison between phenolic and non-phenolic C ₆ -C ₂ -type model compounds

Cited by 4 publications

References 16 publications

Chemicals from lignin by diol-stabilized acidolysis: reaction pathways and kinetics

Chemicals from lignin by diol-stabilized acidolysis: reaction pathways and kinetics

Revisiting the mechanism of β - O -4 bond cleavage during acidolysis of lignin. Part 9: Comprehensive results for guaiacyl-type compounds and the difference in participation mode of bromide and chloride anions between C ₆ -C ₃ -type and C ₆ -C ₂ -type compounds

Revisiting the mechanism of β-O-4 bond cleavage during acidolysis of lignin part 10: reactions of C6–C2-type non-phenolic syringyl model compounds and comparison of the reactions with those of the guaiacyl analogues

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Revisiting the mechanism of β - O -4 bond cleavage during acidolysis of lignin. Part 8: Comparison between phenolic and non-phenolic C 6 -C 2 -type model compounds

Cited by 4 publications

References 16 publications

Chemicals from lignin by diol-stabilized acidolysis: reaction pathways and kinetics

Chemicals from lignin by diol-stabilized acidolysis: reaction pathways and kinetics

Revisiting the mechanism of β - O -4 bond cleavage during acidolysis of lignin. Part 9: Comprehensive results for guaiacyl-type compounds and the difference in participation mode of bromide and chloride anions between C 6 -C 3 -type and C 6 -C 2 -type compounds

Revisiting the mechanism of β-O-4 bond cleavage during acidolysis of lignin part 10: reactions of C6–C2-type non-phenolic syringyl model compounds and comparison of the reactions with those of the guaiacyl analogues

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Revisiting the mechanism of β - O -4 bond cleavage during acidolysis of lignin. Part 8: Comparison between phenolic and non-phenolic C ₆ -C ₂ -type model compounds

Revisiting the mechanism of β - O -4 bond cleavage during acidolysis of lignin. Part 9: Comprehensive results for guaiacyl-type compounds and the difference in participation mode of bromide and chloride anions between C ₆ -C ₃ -type and C ₆ -C ₂ -type compounds