Revisiting the mechanism of β-O-4 bond cleavage during acidolysis of lignin VII: acidolyses of non-phenolic $ C_{6} $-$ C_{2} $-type model compounds using HBr, HCl and $ H_{2} %$ SO_{4} $, and a proposal on the characteristic action of $ Br^{−} $ and $ Cl^{−} $

Abstract A non-phenolic $ C_{6} $-$ C_{2} $-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 $ H_{2} %$ SO_{4} $ with a concentration of 0.2 mol/L at 85 ℃ to examine the differen...
Ausführliche Beschreibung

Gespeichert in:

Autor*in:	Ye, Qiaoqiao [verfasserIn] Yokoyama, Tomoya [verfasserIn]

Format:	E-Artikel
Sprache:	Englisch

Erschienen:	2020

Schlagwörter:	Acid hydrolysis Acid rearrangement Hydrobromic acid Hydrochloric acid Sulfuric acid

Übergeordnetes Werk:	Enthalten in: Journal of wood science - Tokyo : Springer, 1998, 66(2020), 1 vom: 19. Nov.
Übergeordnetes Werk:	volume:66 ; year:2020 ; number:1 ; day:19 ; month:11

Links:	Volltext

DOI / URN:	10.1186/s10086-020-01928-6

Katalog-ID:	SPR04208914X

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520			\|a Abstract A non-phenolic $ C_{6} $-$ C_{2} $-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 $ H_{2} %$ SO_{4} $ with a concentration of 0.2 mol/L at 85 ℃ to examine the differences between these acidolyses. 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 >> $ H_{2} %$ SO_{4} $). Acidolyses of compound II using these acids under the same conditions showed a similar tendency, but the rate differences were much smaller than in the acidolyses of compound I. Acidolyses 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 acidolyses 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.
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author_variant	q y qy t y ty
matchkey_str	article:16114663:2020----::eiiighmcaimf4odlaaeuigcdlssfinniaioyeonnhnlc_c2yeoecmonssnhrcad_s_
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allfields	10.1186/s10086-020-01928-6 doi (DE-627)SPR04208914X (SPR)s10086-020-01928-6-e DE-627 ger DE-627 rakwb eng 660 670 ASE Ye, Qiaoqiao verfasserin aut Revisiting the mechanism of β-O-4 bond cleavage during acidolysis of lignin VII: acidolyses of non-phenolic $ C_{6} $-$ C_{2} $-type model compounds using HBr, HCl and $ H_{2} %$ SO_{4} $, and a proposal on the characteristic action of $ Br^{−} $ and $ Cl^{−} $ 2020 Text txt rdacontent Computermedien c rdamedia Online-Ressource cr rdacarrier Abstract A non-phenolic $ C_{6} $-$ C_{2} $-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 $ H_{2} %$ SO_{4} $ with a concentration of 0.2 mol/L at 85 ℃ to examine the differences between these acidolyses. 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 >> $ H_{2} %$ SO_{4} $). Acidolyses of compound II using these acids under the same conditions showed a similar tendency, but the rate differences were much smaller than in the acidolyses of compound I. Acidolyses 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 acidolyses 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. Acid hydrolysis (dpeaa)DE-He213 Acid rearrangement (dpeaa)DE-He213 Hydrobromic acid (dpeaa)DE-He213 Hydrochloric acid (dpeaa)DE-He213 Sulfuric acid (dpeaa)DE-He213 Yokoyama, Tomoya verfasserin aut Enthalten in Journal of wood science Tokyo : Springer, 1998 66(2020), 1 vom: 19. Nov. (DE-627)300186010 (DE-600)1481666-0 1611-4663 nnns volume:66 year:2020 number:1 day:19 month:11 https://dx.doi.org/10.1186/s10086-020-01928-6 kostenfrei Volltext GBV_USEFLAG_A SYSFLAG_A GBV_SPRINGER SSG-OLC-PHA SSG-OPC-FOR SSG-OPC-ASE GBV_ILN_20 GBV_ILN_22 GBV_ILN_23 GBV_ILN_24 GBV_ILN_31 GBV_ILN_39 GBV_ILN_40 GBV_ILN_60 GBV_ILN_62 GBV_ILN_63 GBV_ILN_65 GBV_ILN_69 GBV_ILN_70 GBV_ILN_73 GBV_ILN_95 GBV_ILN_105 GBV_ILN_110 GBV_ILN_150 GBV_ILN_151 GBV_ILN_161 GBV_ILN_170 GBV_ILN_230 GBV_ILN_285 GBV_ILN_293 GBV_ILN_370 GBV_ILN_602 GBV_ILN_702 GBV_ILN_2005 GBV_ILN_2014 GBV_ILN_2027 GBV_ILN_2190 GBV_ILN_2522 GBV_ILN_2542 GBV_ILN_4012 GBV_ILN_4037 GBV_ILN_4112 GBV_ILN_4125 GBV_ILN_4126 GBV_ILN_4249 GBV_ILN_4305 GBV_ILN_4306 GBV_ILN_4307 GBV_ILN_4313 GBV_ILN_4322 GBV_ILN_4323 GBV_ILN_4324 GBV_ILN_4325 GBV_ILN_4338 GBV_ILN_4367 GBV_ILN_4700 AR 66 2020 1 19 11
spelling	10.1186/s10086-020-01928-6 doi (DE-627)SPR04208914X (SPR)s10086-020-01928-6-e DE-627 ger DE-627 rakwb eng 660 670 ASE Ye, Qiaoqiao verfasserin aut Revisiting the mechanism of β-O-4 bond cleavage during acidolysis of lignin VII: acidolyses of non-phenolic $ C_{6} $-$ C_{2} $-type model compounds using HBr, HCl and $ H_{2} %$ SO_{4} $, and a proposal on the characteristic action of $ Br^{−} $ and $ Cl^{−} $ 2020 Text txt rdacontent Computermedien c rdamedia Online-Ressource cr rdacarrier Abstract A non-phenolic $ C_{6} $-$ C_{2} $-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 $ H_{2} %$ SO_{4} $ with a concentration of 0.2 mol/L at 85 ℃ to examine the differences between these acidolyses. 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 >> $ H_{2} %$ SO_{4} $). Acidolyses of compound II using these acids under the same conditions showed a similar tendency, but the rate differences were much smaller than in the acidolyses of compound I. Acidolyses 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 acidolyses 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. Acid hydrolysis (dpeaa)DE-He213 Acid rearrangement (dpeaa)DE-He213 Hydrobromic acid (dpeaa)DE-He213 Hydrochloric acid (dpeaa)DE-He213 Sulfuric acid (dpeaa)DE-He213 Yokoyama, Tomoya verfasserin aut Enthalten in Journal of wood science Tokyo : Springer, 1998 66(2020), 1 vom: 19. Nov. (DE-627)300186010 (DE-600)1481666-0 1611-4663 nnns volume:66 year:2020 number:1 day:19 month:11 https://dx.doi.org/10.1186/s10086-020-01928-6 kostenfrei Volltext GBV_USEFLAG_A SYSFLAG_A GBV_SPRINGER SSG-OLC-PHA SSG-OPC-FOR SSG-OPC-ASE GBV_ILN_20 GBV_ILN_22 GBV_ILN_23 GBV_ILN_24 GBV_ILN_31 GBV_ILN_39 GBV_ILN_40 GBV_ILN_60 GBV_ILN_62 GBV_ILN_63 GBV_ILN_65 GBV_ILN_69 GBV_ILN_70 GBV_ILN_73 GBV_ILN_95 GBV_ILN_105 GBV_ILN_110 GBV_ILN_150 GBV_ILN_151 GBV_ILN_161 GBV_ILN_170 GBV_ILN_230 GBV_ILN_285 GBV_ILN_293 GBV_ILN_370 GBV_ILN_602 GBV_ILN_702 GBV_ILN_2005 GBV_ILN_2014 GBV_ILN_2027 GBV_ILN_2190 GBV_ILN_2522 GBV_ILN_2542 GBV_ILN_4012 GBV_ILN_4037 GBV_ILN_4112 GBV_ILN_4125 GBV_ILN_4126 GBV_ILN_4249 GBV_ILN_4305 GBV_ILN_4306 GBV_ILN_4307 GBV_ILN_4313 GBV_ILN_4322 GBV_ILN_4323 GBV_ILN_4324 GBV_ILN_4325 GBV_ILN_4338 GBV_ILN_4367 GBV_ILN_4700 AR 66 2020 1 19 11
allfields_unstemmed	10.1186/s10086-020-01928-6 doi (DE-627)SPR04208914X (SPR)s10086-020-01928-6-e DE-627 ger DE-627 rakwb eng 660 670 ASE Ye, Qiaoqiao verfasserin aut Revisiting the mechanism of β-O-4 bond cleavage during acidolysis of lignin VII: acidolyses of non-phenolic $ C_{6} $-$ C_{2} $-type model compounds using HBr, HCl and $ H_{2} %$ SO_{4} $, and a proposal on the characteristic action of $ Br^{−} $ and $ Cl^{−} $ 2020 Text txt rdacontent Computermedien c rdamedia Online-Ressource cr rdacarrier Abstract A non-phenolic $ C_{6} $-$ C_{2} $-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 $ H_{2} %$ SO_{4} $ with a concentration of 0.2 mol/L at 85 ℃ to examine the differences between these acidolyses. 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 >> $ H_{2} %$ SO_{4} $). Acidolyses of compound II using these acids under the same conditions showed a similar tendency, but the rate differences were much smaller than in the acidolyses of compound I. Acidolyses 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 acidolyses 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. Acid hydrolysis (dpeaa)DE-He213 Acid rearrangement (dpeaa)DE-He213 Hydrobromic acid (dpeaa)DE-He213 Hydrochloric acid (dpeaa)DE-He213 Sulfuric acid (dpeaa)DE-He213 Yokoyama, Tomoya verfasserin aut Enthalten in Journal of wood science Tokyo : Springer, 1998 66(2020), 1 vom: 19. Nov. (DE-627)300186010 (DE-600)1481666-0 1611-4663 nnns volume:66 year:2020 number:1 day:19 month:11 https://dx.doi.org/10.1186/s10086-020-01928-6 kostenfrei Volltext GBV_USEFLAG_A SYSFLAG_A GBV_SPRINGER SSG-OLC-PHA SSG-OPC-FOR SSG-OPC-ASE GBV_ILN_20 GBV_ILN_22 GBV_ILN_23 GBV_ILN_24 GBV_ILN_31 GBV_ILN_39 GBV_ILN_40 GBV_ILN_60 GBV_ILN_62 GBV_ILN_63 GBV_ILN_65 GBV_ILN_69 GBV_ILN_70 GBV_ILN_73 GBV_ILN_95 GBV_ILN_105 GBV_ILN_110 GBV_ILN_150 GBV_ILN_151 GBV_ILN_161 GBV_ILN_170 GBV_ILN_230 GBV_ILN_285 GBV_ILN_293 GBV_ILN_370 GBV_ILN_602 GBV_ILN_702 GBV_ILN_2005 GBV_ILN_2014 GBV_ILN_2027 GBV_ILN_2190 GBV_ILN_2522 GBV_ILN_2542 GBV_ILN_4012 GBV_ILN_4037 GBV_ILN_4112 GBV_ILN_4125 GBV_ILN_4126 GBV_ILN_4249 GBV_ILN_4305 GBV_ILN_4306 GBV_ILN_4307 GBV_ILN_4313 GBV_ILN_4322 GBV_ILN_4323 GBV_ILN_4324 GBV_ILN_4325 GBV_ILN_4338 GBV_ILN_4367 GBV_ILN_4700 AR 66 2020 1 19 11
allfieldsGer	10.1186/s10086-020-01928-6 doi (DE-627)SPR04208914X (SPR)s10086-020-01928-6-e DE-627 ger DE-627 rakwb eng 660 670 ASE Ye, Qiaoqiao verfasserin aut Revisiting the mechanism of β-O-4 bond cleavage during acidolysis of lignin VII: acidolyses of non-phenolic $ C_{6} $-$ C_{2} $-type model compounds using HBr, HCl and $ H_{2} %$ SO_{4} $, and a proposal on the characteristic action of $ Br^{−} $ and $ Cl^{−} $ 2020 Text txt rdacontent Computermedien c rdamedia Online-Ressource cr rdacarrier Abstract A non-phenolic $ C_{6} $-$ C_{2} $-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 $ H_{2} %$ SO_{4} $ with a concentration of 0.2 mol/L at 85 ℃ to examine the differences between these acidolyses. 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 >> $ H_{2} %$ SO_{4} $). Acidolyses of compound II using these acids under the same conditions showed a similar tendency, but the rate differences were much smaller than in the acidolyses of compound I. Acidolyses 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 acidolyses 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. Acid hydrolysis (dpeaa)DE-He213 Acid rearrangement (dpeaa)DE-He213 Hydrobromic acid (dpeaa)DE-He213 Hydrochloric acid (dpeaa)DE-He213 Sulfuric acid (dpeaa)DE-He213 Yokoyama, Tomoya verfasserin aut Enthalten in Journal of wood science Tokyo : Springer, 1998 66(2020), 1 vom: 19. Nov. (DE-627)300186010 (DE-600)1481666-0 1611-4663 nnns volume:66 year:2020 number:1 day:19 month:11 https://dx.doi.org/10.1186/s10086-020-01928-6 kostenfrei Volltext GBV_USEFLAG_A SYSFLAG_A GBV_SPRINGER SSG-OLC-PHA SSG-OPC-FOR SSG-OPC-ASE GBV_ILN_20 GBV_ILN_22 GBV_ILN_23 GBV_ILN_24 GBV_ILN_31 GBV_ILN_39 GBV_ILN_40 GBV_ILN_60 GBV_ILN_62 GBV_ILN_63 GBV_ILN_65 GBV_ILN_69 GBV_ILN_70 GBV_ILN_73 GBV_ILN_95 GBV_ILN_105 GBV_ILN_110 GBV_ILN_150 GBV_ILN_151 GBV_ILN_161 GBV_ILN_170 GBV_ILN_230 GBV_ILN_285 GBV_ILN_293 GBV_ILN_370 GBV_ILN_602 GBV_ILN_702 GBV_ILN_2005 GBV_ILN_2014 GBV_ILN_2027 GBV_ILN_2190 GBV_ILN_2522 GBV_ILN_2542 GBV_ILN_4012 GBV_ILN_4037 GBV_ILN_4112 GBV_ILN_4125 GBV_ILN_4126 GBV_ILN_4249 GBV_ILN_4305 GBV_ILN_4306 GBV_ILN_4307 GBV_ILN_4313 GBV_ILN_4322 GBV_ILN_4323 GBV_ILN_4324 GBV_ILN_4325 GBV_ILN_4338 GBV_ILN_4367 GBV_ILN_4700 AR 66 2020 1 19 11
allfieldsSound	10.1186/s10086-020-01928-6 doi (DE-627)SPR04208914X (SPR)s10086-020-01928-6-e DE-627 ger DE-627 rakwb eng 660 670 ASE Ye, Qiaoqiao verfasserin aut Revisiting the mechanism of β-O-4 bond cleavage during acidolysis of lignin VII: acidolyses of non-phenolic $ C_{6} $-$ C_{2} $-type model compounds using HBr, HCl and $ H_{2} %$ SO_{4} $, and a proposal on the characteristic action of $ Br^{−} $ and $ Cl^{−} $ 2020 Text txt rdacontent Computermedien c rdamedia Online-Ressource cr rdacarrier Abstract A non-phenolic $ C_{6} $-$ C_{2} $-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 $ H_{2} %$ SO_{4} $ with a concentration of 0.2 mol/L at 85 ℃ to examine the differences between these acidolyses. 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 >> $ H_{2} %$ SO_{4} $). Acidolyses of compound II using these acids under the same conditions showed a similar tendency, but the rate differences were much smaller than in the acidolyses of compound I. Acidolyses 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 acidolyses 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. Acid hydrolysis (dpeaa)DE-He213 Acid rearrangement (dpeaa)DE-He213 Hydrobromic acid (dpeaa)DE-He213 Hydrochloric acid (dpeaa)DE-He213 Sulfuric acid (dpeaa)DE-He213 Yokoyama, Tomoya verfasserin aut Enthalten in Journal of wood science Tokyo : Springer, 1998 66(2020), 1 vom: 19. Nov. (DE-627)300186010 (DE-600)1481666-0 1611-4663 nnns volume:66 year:2020 number:1 day:19 month:11 https://dx.doi.org/10.1186/s10086-020-01928-6 kostenfrei Volltext GBV_USEFLAG_A SYSFLAG_A GBV_SPRINGER SSG-OLC-PHA SSG-OPC-FOR SSG-OPC-ASE GBV_ILN_20 GBV_ILN_22 GBV_ILN_23 GBV_ILN_24 GBV_ILN_31 GBV_ILN_39 GBV_ILN_40 GBV_ILN_60 GBV_ILN_62 GBV_ILN_63 GBV_ILN_65 GBV_ILN_69 GBV_ILN_70 GBV_ILN_73 GBV_ILN_95 GBV_ILN_105 GBV_ILN_110 GBV_ILN_150 GBV_ILN_151 GBV_ILN_161 GBV_ILN_170 GBV_ILN_230 GBV_ILN_285 GBV_ILN_293 GBV_ILN_370 GBV_ILN_602 GBV_ILN_702 GBV_ILN_2005 GBV_ILN_2014 GBV_ILN_2027 GBV_ILN_2190 GBV_ILN_2522 GBV_ILN_2542 GBV_ILN_4012 GBV_ILN_4037 GBV_ILN_4112 GBV_ILN_4125 GBV_ILN_4126 GBV_ILN_4249 GBV_ILN_4305 GBV_ILN_4306 GBV_ILN_4307 GBV_ILN_4313 GBV_ILN_4322 GBV_ILN_4323 GBV_ILN_4324 GBV_ILN_4325 GBV_ILN_4338 GBV_ILN_4367 GBV_ILN_4700 AR 66 2020 1 19 11
language	English
source	Enthalten in Journal of wood science 66(2020), 1 vom: 19. Nov. volume:66 year:2020 number:1 day:19 month:11
sourceStr	Enthalten in Journal of wood science 66(2020), 1 vom: 19. Nov. volume:66 year:2020 number:1 day:19 month:11
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institution	findex.gbv.de
topic_facet	Acid hydrolysis Acid rearrangement Hydrobromic acid Hydrochloric acid Sulfuric acid
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container_title	Journal of wood science
authorswithroles_txt_mv	Ye, Qiaoqiao @@aut@@ Yokoyama, Tomoya @@aut@@
publishDateDaySort_date	2020-11-19T00:00:00Z
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author	Ye, Qiaoqiao
spellingShingle	Ye, Qiaoqiao ddc 660 misc Acid hydrolysis misc Acid rearrangement misc Hydrobromic acid misc Hydrochloric acid misc Sulfuric acid Revisiting the mechanism of β-O-4 bond cleavage during acidolysis of lignin VII: acidolyses of non-phenolic $ C_{6} $-$ C_{2} $-type model compounds using HBr, HCl and $ H_{2} %$ SO_{4} $, and a proposal on the characteristic action of $ Br^{−} $ and $ Cl^{−} $
authorStr	Ye, Qiaoqiao
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issn	1611-4663
topic_title	660 670 ASE Revisiting the mechanism of β-O-4 bond cleavage during acidolysis of lignin VII: acidolyses of non-phenolic $ C_{6} $-$ C_{2} $-type model compounds using HBr, HCl and $ H_{2} %$ SO_{4} $, and a proposal on the characteristic action of $ Br^{−} $ and $ Cl^{−} $ Acid hydrolysis (dpeaa)DE-He213 Acid rearrangement (dpeaa)DE-He213 Hydrobromic acid (dpeaa)DE-He213 Hydrochloric acid (dpeaa)DE-He213 Sulfuric acid (dpeaa)DE-He213
topic	ddc 660 misc Acid hydrolysis misc Acid rearrangement misc Hydrobromic acid misc Hydrochloric acid misc Sulfuric acid
topic_unstemmed	ddc 660 misc Acid hydrolysis misc Acid rearrangement misc Hydrobromic acid misc Hydrochloric acid misc Sulfuric acid
topic_browse	ddc 660 misc Acid hydrolysis misc Acid rearrangement misc Hydrobromic acid misc Hydrochloric acid misc Sulfuric acid
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title	Revisiting the mechanism of β-O-4 bond cleavage during acidolysis of lignin VII: acidolyses of non-phenolic $ C_{6} $-$ C_{2} $-type model compounds using HBr, HCl and $ H_{2} %$ SO_{4} $, and a proposal on the characteristic action of $ Br^{−} $ and $ Cl^{−} $
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title_full	Revisiting the mechanism of β-O-4 bond cleavage during acidolysis of lignin VII: acidolyses of non-phenolic $ C_{6} $-$ C_{2} $-type model compounds using HBr, HCl and $ H_{2} %$ SO_{4} $, and a proposal on the characteristic action of $ Br^{−} $ and $ Cl^{−} $
author_sort	Ye, Qiaoqiao
journal	Journal of wood science
journalStr	Journal of wood science
lang_code	eng
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dewey-hundreds	600 - Technology
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publishDateSort	2020
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author_browse	Ye, Qiaoqiao Yokoyama, Tomoya
container_volume	66
class	660 670 ASE
format_se	Elektronische Aufsätze
author-letter	Ye, Qiaoqiao
doi_str_mv	10.1186/s10086-020-01928-6
dewey-full	660 670
author2-role	verfasserin
title_sort	revisiting the mechanism of β-o-4 bond cleavage during acidolysis of lignin vii: acidolyses of non-phenolic $ c_{6} $-$ c_{2} $-type model compounds using hbr, hcl and $ h_{2} %$ so_{4} $, and a proposal on the characteristic action of $ br^{−} $ and $ cl^{−} $
title_auth	Revisiting the mechanism of β-O-4 bond cleavage during acidolysis of lignin VII: acidolyses of non-phenolic $ C_{6} $-$ C_{2} $-type model compounds using HBr, HCl and $ H_{2} %$ SO_{4} $, and a proposal on the characteristic action of $ Br^{−} $ and $ Cl^{−} $
abstract	Abstract A non-phenolic $ C_{6} $-$ C_{2} $-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 $ H_{2} %$ SO_{4} $ with a concentration of 0.2 mol/L at 85 ℃ to examine the differences between these acidolyses. 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 >> $ H_{2} %$ SO_{4} $). Acidolyses of compound II using these acids under the same conditions showed a similar tendency, but the rate differences were much smaller than in the acidolyses of compound I. Acidolyses 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 acidolyses 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.
abstractGer	Abstract A non-phenolic $ C_{6} $-$ C_{2} $-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 $ H_{2} %$ SO_{4} $ with a concentration of 0.2 mol/L at 85 ℃ to examine the differences between these acidolyses. 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 >> $ H_{2} %$ SO_{4} $). Acidolyses of compound II using these acids under the same conditions showed a similar tendency, but the rate differences were much smaller than in the acidolyses of compound I. Acidolyses 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 acidolyses 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.
abstract_unstemmed	Abstract A non-phenolic $ C_{6} $-$ C_{2} $-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 $ H_{2} %$ SO_{4} $ with a concentration of 0.2 mol/L at 85 ℃ to examine the differences between these acidolyses. 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 >> $ H_{2} %$ SO_{4} $). Acidolyses of compound II using these acids under the same conditions showed a similar tendency, but the rate differences were much smaller than in the acidolyses of compound I. Acidolyses 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 acidolyses 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.
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container_issue	1
title_short	Revisiting the mechanism of β-O-4 bond cleavage during acidolysis of lignin VII: acidolyses of non-phenolic $ C_{6} $-$ C_{2} $-type model compounds using HBr, HCl and $ H_{2} %$ SO_{4} $, and a proposal on the characteristic action of $ Br^{−} $ and $ Cl^{−} $
url	https://dx.doi.org/10.1186/s10086-020-01928-6
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up_date	2024-07-04T00:46:09.279Z
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Revisiting the mechanism of β-O-4 bond cleavage during acidolysis of lignin VII: acidolyses of non-phenolic $ C_{6} $-$ C_{2} $-type model compounds using HBr, HCl and $ H_{2} %$ SO_{4} $, and a proposal on the characteristic action of $ Br^{−} $ and $ Cl^{−} $

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