Russian Chemical Bulletin, volume 62, issue 11, pages 2407-2423

Reaction of donor-acceptor cyclopropanes with 1,3-diphenylisobenzofuran. Lewis acid effect on the reaction pathway

Publication typeJournal Article
Publication date2013-11-01
Quartile SCImago
Q3
Quartile WOS
Q3
Impact factor1.7
ISSN10665285, 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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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.
GOST all authors (up to 50) Copy
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.
RIS |
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RIS Copy
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 00:00:00
PB - Springer Nature
SP - 2407-2423
IS - 11
VL - 62
SN - 1066-5285
SN - 1573-9171
ER -
BibTex |
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BibTex Copy
@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}
}
MLA
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MLA Copy
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.
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