Angewandte Chemie - International Edition, volume 47, issue 6, pages 1107-1110
Donor–Acceptor Cyclopropanes as Three-Carbon Components in a [4+3] Cycloaddition Reaction with 1,3-Diphenylisobenzofuran
Publication type: Journal Article
Publication date: 2008-01-25
Quartile SCImago
Q1
Quartile WOS
Q1
Impact factor: 16.6
ISSN: 14337851, 15213773
General Chemistry
Catalysis
Abstract
Substituted cyclopropanes have found broad application in modern organic synthesis owing to the unique reactivity of the cyclopropane moiety. Cyclopropanes can often be considered as three-carbon analogues of C=C bonds. For example, alkenes and cyclopropanes react with strong electrophiles and various radicals. Both undergo the addition of hydrogen and can be oxidized at the a position. The reactivity of cyclopropanes with electron-withdrawing substituents is similar to that of electron-deficient alkenes. However, the cycloaddition reactions of alkenes and cyclopropanes are quite different. In particular, the thermal reactions of alkenes are represented mainly by [1+2], [3+2], and [4+2] cycloaddition processes; thermal [2+2] cycloaddition occurs in very specific cases only. In contrast, the most well known type of cyclopropane cycloaddition is the [2p + 2s] reaction with alkenes. As this reaction yields cyclopentanes, it can also be considered as a [2+3] cycloaddition. The scope of such [2+3] cycloaddition reactions has been expanded significantly through the use of donor–acceptor cyclopropanes. The presence of both electron-donating and electron-withdrawing substituents on the cyclopropane ring enables cycloaddition to various multiple bonds, including C=C, C=O, C=N, and C N bonds. The [4+3] cycloaddition of cyclopropanes with dienes (Scheme 1) has not been reported previously, although this
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Ivanova O. et al. Donor–Acceptor Cyclopropanes as Three-Carbon Components in a [4+3] Cycloaddition Reaction with 1,3-Diphenylisobenzofuran // Angewandte Chemie - International Edition. 2008. Vol. 47. No. 6. pp. 1107-1110.
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Ivanova O., Budynina E. M., Grishin Y., Trushkov I. V., Verteletskii P. V. Donor–Acceptor Cyclopropanes as Three-Carbon Components in a [4+3] Cycloaddition Reaction with 1,3-Diphenylisobenzofuran // Angewandte Chemie - International Edition. 2008. Vol. 47. No. 6. pp. 1107-1110.
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TY - JOUR
DO - 10.1002/anie.200704438
UR - https://doi.org/10.1002/anie.200704438
TI - Donor–Acceptor Cyclopropanes as Three-Carbon Components in a [4+3] Cycloaddition Reaction with 1,3-Diphenylisobenzofuran
T2 - Angewandte Chemie - International Edition
AU - Ivanova, Olga
AU - Budynina, Ekaterina M
AU - Grishin, Yuri
AU - Trushkov, Igor V
AU - Verteletskii, Pavel V
PY - 2008
DA - 2008/01/25 00:00:00
PB - Wiley
SP - 1107-1110
IS - 6
VL - 47
SN - 1433-7851
SN - 1521-3773
ER -
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@article{2008_Ivanova,
author = {Olga Ivanova and Ekaterina M Budynina and Yuri Grishin and Igor V Trushkov and Pavel V Verteletskii},
title = {Donor–Acceptor Cyclopropanes as Three-Carbon Components in a [4+3] Cycloaddition Reaction with 1,3-Diphenylisobenzofuran},
journal = {Angewandte Chemie - International Edition},
year = {2008},
volume = {47},
publisher = {Wiley},
month = {jan},
url = {https://doi.org/10.1002/anie.200704438},
number = {6},
pages = {1107--1110},
doi = {10.1002/anie.200704438}
}
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Ivanova, Olga, et al. “Donor–Acceptor Cyclopropanes as Three-Carbon Components in a [4+3] Cycloaddition Reaction with 1,3-Diphenylisobenzofuran.” Angewandte Chemie - International Edition, vol. 47, no. 6, Jan. 2008, pp. 1107-1110. https://doi.org/10.1002/anie.200704438.