Reaction of donor-acceptor cyclopropanes with 1,3-diphenylisobenzofuran. Lewis acid effect on the reaction pathway
Publication type: Journal Article
Publication date: 2013-11-01
scimago Q3
SJR: 0.305
CiteScore: 2.8
Impact factor: —
ISSN: 10665285, 15739171
General Chemistry
Abstract
Reaction of donor-acceptor cyclopropanes with 1,3-diphenylisobenzofuran in the presence of lanthanide triflates, as well as CuOTf, Sn(OTf)2, SnCl2, ZnCl2, GaCl3, and MgI2, proceeds as a formal [3+4]-cycloaddition leading to a newly formed seven-membered ring. This reaction was found to be typical of cyclopropane-1,1-diesters and dinitriles, as well as 1-nitrocyclo-propanecarboxylates containing aromatic, heteroaromatic, and vinylic substituents at the C(2) atom of the small ring. When Me3SiOTf, TiCl4, SnCl4, or BF3·OEt2 were used as initiators, unusual cyclic hemiacetals were formed via the conjugate 1,4-addition of a cyclopropane and a nucleophile to the diene moiety.
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Total citations:
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Citations from 2024:
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Chagarovskiy A. O. et al. Reaction of donor-acceptor cyclopropanes with 1,3-diphenylisobenzofuran. Lewis acid effect on the reaction pathway // Russian Chemical Bulletin. 2013. Vol. 62. No. 11. pp. 2407-2423.
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Chagarovskiy A. O., Ivanova O. A., Budynina E. M., Kolychev E. L., Nechaev M. S., Trushkov I. V., Melnikov M. Ya. Reaction of donor-acceptor cyclopropanes with 1,3-diphenylisobenzofuran. Lewis acid effect on the reaction pathway // Russian Chemical Bulletin. 2013. Vol. 62. No. 11. pp. 2407-2423.
Cite this
RIS
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TY - JOUR
DO - 10.1007/s11172-013-0349-x
UR - https://doi.org/10.1007/s11172-013-0349-x
TI - Reaction of donor-acceptor cyclopropanes with 1,3-diphenylisobenzofuran. Lewis acid effect on the reaction pathway
T2 - Russian Chemical Bulletin
AU - Chagarovskiy, A O
AU - Ivanova, O. A.
AU - Budynina, E M
AU - Kolychev, E L
AU - Nechaev, M S
AU - Trushkov, I V
AU - Melnikov, M Ya
PY - 2013
DA - 2013/11/01
PB - Springer Nature
SP - 2407-2423
IS - 11
VL - 62
SN - 1066-5285
SN - 1573-9171
ER -
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BibTex (up to 50 authors)
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@article{2013_Chagarovskiy,
author = {A O Chagarovskiy and O. A. Ivanova and E M Budynina and E L Kolychev and M S Nechaev and I V Trushkov and M Ya Melnikov},
title = {Reaction of donor-acceptor cyclopropanes with 1,3-diphenylisobenzofuran. Lewis acid effect on the reaction pathway},
journal = {Russian Chemical Bulletin},
year = {2013},
volume = {62},
publisher = {Springer Nature},
month = {nov},
url = {https://doi.org/10.1007/s11172-013-0349-x},
number = {11},
pages = {2407--2423},
doi = {10.1007/s11172-013-0349-x}
}
Cite this
MLA
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Chagarovskiy, A. O., et al. “Reaction of donor-acceptor cyclopropanes with 1,3-diphenylisobenzofuran. Lewis acid effect on the reaction pathway.” Russian Chemical Bulletin, vol. 62, no. 11, Nov. 2013, pp. 2407-2423. https://doi.org/10.1007/s11172-013-0349-x.