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Laccase-catalyzed phenol oxidation. Rapid assignment of ring-proton deficient polycyclic benzofuran regioisomers by experimental 1H–13C long-range coupling constants and DFT-predicted product formation

Тип публикацииJournal Article
Дата публикации2011-02-02
scimago Q2
wos Q2
БС1
SJR0.6
CiteScore5.2
Impact factor2.7
ISSN14770520, 14770539
Organic Chemistry
Biochemistry
Physical and Theoretical Chemistry
Краткое описание
Laccase-catalyzed oxidation of substituted catechols followed by reaction with 4-hydroxy-pyrone/-benzopyrone afforded substituted benzofuran regioisomers whose structures with only two aromatic protons in total prevent a rapid structural assignment. Based on the evaluation of (1)H-(13)C long-range coupling constants a rule of thumb could be deduced for an easy and unambiguous differentiation between the possible regioisomers formed. DFT frontier orbital calculations of the reactants offer an interesting tool to explain the regioselectivity of the key reaction.
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ГОСТ |
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Leutbecher H. et al. Laccase-catalyzed phenol oxidation. Rapid assignment of ring-proton deficient polycyclic benzofuran regioisomers by experimental 1H–13C long-range coupling constants and DFT-predicted product formation // Organic and Biomolecular Chemistry. 2011. Vol. 9. No. 8. p. 2667.
ГОСТ со всеми авторами (до 50) Скопировать
Leutbecher H., GREINER G., Amann R., Stolz A., Beifuss U., Conrad J. Laccase-catalyzed phenol oxidation. Rapid assignment of ring-proton deficient polycyclic benzofuran regioisomers by experimental 1H–13C long-range coupling constants and DFT-predicted product formation // Organic and Biomolecular Chemistry. 2011. Vol. 9. No. 8. p. 2667.
RIS |
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TY - JOUR
DO - 10.1039/c1ob00012h
UR - https://doi.org/10.1039/c1ob00012h
TI - Laccase-catalyzed phenol oxidation. Rapid assignment of ring-proton deficient polycyclic benzofuran regioisomers by experimental 1H–13C long-range coupling constants and DFT-predicted product formation
T2 - Organic and Biomolecular Chemistry
AU - Leutbecher, Heiko
AU - GREINER, GERHARD
AU - Amann, Robert
AU - Stolz, A.
AU - Beifuss, Uwe
AU - Conrad, JÜrgen
PY - 2011
DA - 2011/02/02
PB - Royal Society of Chemistry (RSC)
SP - 2667
IS - 8
VL - 9
PMID - 21369581
SN - 1477-0520
SN - 1477-0539
ER -
BibTex |
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BibTex (до 50 авторов) Скопировать
@article{2011_Leutbecher,
author = {Heiko Leutbecher and GERHARD GREINER and Robert Amann and A. Stolz and Uwe Beifuss and JÜrgen Conrad},
title = {Laccase-catalyzed phenol oxidation. Rapid assignment of ring-proton deficient polycyclic benzofuran regioisomers by experimental 1H–13C long-range coupling constants and DFT-predicted product formation},
journal = {Organic and Biomolecular Chemistry},
year = {2011},
volume = {9},
publisher = {Royal Society of Chemistry (RSC)},
month = {feb},
url = {https://doi.org/10.1039/c1ob00012h},
number = {8},
pages = {2667},
doi = {10.1039/c1ob00012h}
}
MLA
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Leutbecher, Heiko, et al. “Laccase-catalyzed phenol oxidation. Rapid assignment of ring-proton deficient polycyclic benzofuran regioisomers by experimental 1H–13C long-range coupling constants and DFT-predicted product formation.” Organic and Biomolecular Chemistry, vol. 9, no. 8, Feb. 2011, p. 2667. https://doi.org/10.1039/c1ob00012h.