On December 31, 2020, Ye, Qiaoqiao; Yokoyama, Tomoya published an article.Electric Literature of 91-16-7 The title of the article was Revisiting the mechanism of β-O-4 bond cleavage during acidolysis of lignin VII: acidolyses of non-phenolic C6-C2-type model compounds using HBr, HCl and H2SO4, and a proposal on the characteristic action of Br- and Cl-. And the article contained the following:
A non-phenolic C6-C2-type lignin model compound with the β-O-4 bond, 2-(2-methoxyphenoxy)-1-(3,4-dimethoxyphenyl)ethanol (I), was acidolyzed in aqueous 82% 1,4-dioxane containing HBr, HCl, or H2SO4 with a concentration of 0.2 mol/L at 85°C to examine the differences between these acidolyzes. Compound I primarily converted to an enol ether compound, 1-(2-methoxyphenoxy)-2-(3,4-dimethoxyphenyl)ethene (II), via the benzyl cation followed by acidolytic β-O-4 bond cleavage regardless of the acid-type, although the disappearance rates of compound I were remarkably different (HBr > HCl >> H2SO4). Acidolyzes of compound II using these acids under the same conditions showed a similar tendency, but the rate differences were much smaller than in the acidolyzes of compound I. Acidolyzes of the α-methyl-etherified derivative of compound I (I-α-OMe) using these acids under the same conditions suggested that the formation rates of the benzyl cation from compound I-α-OMe (also from compound I) are not largely different between the acidolyzes using these acids, but those of compound II from the benzyl cation are remarkably different. Acidolysis of the α-bromo-substituting derivative of compound I (I-α-Br) using HBr under the same conditions showed a characteristic action of Br in the acidolysis. Br adds to the benzyl cation generated from compound I or I-α-OMe to afford unstable compound I-α-Br, resulting in acceleration of the formation of compound II and of the whole acidolysis reaction. The experimental process involved the reaction of 1,2-Dimethoxybenzene(cas: 91-16-7).Electric Literature of 91-16-7
The Article related to lignin acid hydrolysis reaction mechanism bond cleavage, Physical Organic Chemistry: Ring Formation, Cleavage, Enlargement, and Contraction and other aspects.Electric Literature of 91-16-7
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Ether | (C2H5)2O – PubChem