Dehydrobenzene in the Reaction of a Tandem [4+2]/[4+2] Cycloaddition with Linear bis-furyldienes
Publication type: Journal Article
Publication date: 2021-09-01
scimago Q4
wos Q4
SJR: 0.243
CiteScore: 2.7
Impact factor: 1.0
ISSN: 00093122, 15738353
Organic Chemistry
Abstract
Tandem [4+2]/[4+2] cycloaddition between bis-dienes containing two furan rings and dehydrobenzene as a dienophile was studied. It was shown that dehydrobenzene generated in situ from 2-(trimethylsilyl)phenyl trifluoromethanesulfonate is capable of a facile intermolecular [4+2] cycloaddition to a furan moiety of a diene at room temperature. The next step, that involves intramolecular Diels–Alder reaction (the IMDAF reaction) with the second furan ring, requires elevated temperature up to 80°С. It has been shown that even under optimal conditions the yields of the target annulated 1,4:5,8-diepoxynaphthalenes do not exceed 50%. The main byproducts are double cycloaddition adducts formed during the interaction of two aryne subunits with both furan rings of the initial bis-diene.
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Kvyatkovskaya E. A. et al. Dehydrobenzene in the Reaction of a Tandem [4+2]/[4+2] Cycloaddition with Linear bis-furyldienes // Chemistry of Heterocyclic Compounds. 2021. Vol. 57. No. 9. pp. 949-961.
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Kvyatkovskaya E. A., Epifanova P. P., Borisova K. K., Borovkova S. I., Grigoriev M. S., Zubkov F. I. Dehydrobenzene in the Reaction of a Tandem [4+2]/[4+2] Cycloaddition with Linear bis-furyldienes // Chemistry of Heterocyclic Compounds. 2021. Vol. 57. No. 9. pp. 949-961.
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TY - JOUR
DO - 10.1007/s10593-021-03005-2
UR - https://doi.org/10.1007/s10593-021-03005-2
TI - Dehydrobenzene in the Reaction of a Tandem [4+2]/[4+2] Cycloaddition with Linear bis-furyldienes
T2 - Chemistry of Heterocyclic Compounds
AU - Kvyatkovskaya, Elizaveta A.
AU - Epifanova, Polina P.
AU - Borisova, Kseniya K.
AU - Borovkova, Sophia I
AU - Grigoriev, Mikhail S.
AU - Zubkov, Fedor I.
PY - 2021
DA - 2021/09/01
PB - Springer Nature
SP - 949-961
IS - 9
VL - 57
SN - 0009-3122
SN - 1573-8353
ER -
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@article{2021_Kvyatkovskaya,
author = {Elizaveta A. Kvyatkovskaya and Polina P. Epifanova and Kseniya K. Borisova and Sophia I Borovkova and Mikhail S. Grigoriev and Fedor I. Zubkov},
title = {Dehydrobenzene in the Reaction of a Tandem [4+2]/[4+2] Cycloaddition with Linear bis-furyldienes},
journal = {Chemistry of Heterocyclic Compounds},
year = {2021},
volume = {57},
publisher = {Springer Nature},
month = {sep},
url = {https://doi.org/10.1007/s10593-021-03005-2},
number = {9},
pages = {949--961},
doi = {10.1007/s10593-021-03005-2}
}
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MLA
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Kvyatkovskaya, Elizaveta A., et al. “Dehydrobenzene in the Reaction of a Tandem [4+2]/[4+2] Cycloaddition with Linear bis-furyldienes.” Chemistry of Heterocyclic Compounds, vol. 57, no. 9, Sep. 2021, pp. 949-961. https://doi.org/10.1007/s10593-021-03005-2.