Cycloacylation of chloro-substituted hydroquinone dimethyl ethers with dichloromaleic anhydride
Publication type: Journal Article
Publication date: 2016-04-01
scimago Q3
SJR: 0.305
CiteScore: 2.8
Impact factor: —
ISSN: 10665285, 15739171
General Chemistry
Abstract
Under the drastic conditions of Zahn—Ochwat cycloacylation of 2-chloroand 2,3-dichlorohydroquinones with dichloromaleic anhydride (a melt of anhydrous AlCl3 and NaCl, 185—195 °C), the substrates undergo various degrees of disproportionation, which reduces the yields of the target triand tetrachloronaphthazarins. Quantum chemical calculations showed that the cycloacylation in question proceeds as a double aromatic electrophilic substitution of the vicinal protons with the corresponding oxocarbenium ions (acylium cations).
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Novikov V. L. et al. Cycloacylation of chloro-substituted hydroquinone dimethyl ethers with dichloromaleic anhydride // Russian Chemical Bulletin. 2016. Vol. 65. No. 4. pp. 993-1003.
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Novikov V. L., Balaneva N. N., Shestak O. P., Anufriev V. Ph., Glazunov V. Cycloacylation of chloro-substituted hydroquinone dimethyl ethers with dichloromaleic anhydride // Russian Chemical Bulletin. 2016. Vol. 65. No. 4. pp. 993-1003.
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TY - JOUR
DO - 10.1007/s11172-016-1402-3
UR - https://doi.org/10.1007/s11172-016-1402-3
TI - Cycloacylation of chloro-substituted hydroquinone dimethyl ethers with dichloromaleic anhydride
T2 - Russian Chemical Bulletin
AU - Novikov, V L
AU - Balaneva, N N
AU - Shestak, O P
AU - Anufriev, V Ph
AU - Glazunov, V.P
PY - 2016
DA - 2016/04/01
PB - Springer Nature
SP - 993-1003
IS - 4
VL - 65
SN - 1066-5285
SN - 1573-9171
ER -
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@article{2016_Novikov,
author = {V L Novikov and N N Balaneva and O P Shestak and V Ph Anufriev and V.P Glazunov},
title = {Cycloacylation of chloro-substituted hydroquinone dimethyl ethers with dichloromaleic anhydride},
journal = {Russian Chemical Bulletin},
year = {2016},
volume = {65},
publisher = {Springer Nature},
month = {apr},
url = {https://doi.org/10.1007/s11172-016-1402-3},
number = {4},
pages = {993--1003},
doi = {10.1007/s11172-016-1402-3}
}
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MLA
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Novikov, V. L., et al. “Cycloacylation of chloro-substituted hydroquinone dimethyl ethers with dichloromaleic anhydride.” Russian Chemical Bulletin, vol. 65, no. 4, Apr. 2016, pp. 993-1003. https://doi.org/10.1007/s11172-016-1402-3.