Journal of the American Chemical Society, volume 128, issue 19, pages 6306-6307
PtCl2-Catalyzed Rearrangement of Methylenecyclopropanes
Publication type: Journal Article
Publication date: 2006-04-26
Quartile SCImago
Q1
Quartile WOS
Q1
Impact factor: 15
ISSN: 00027863, 15205126
General Chemistry
Catalysis
Biochemistry
Colloid and Surface Chemistry
Abstract
Alkylidenecyclopropanes readily convert into cyclobutene derivatives on treatment with catalytic amounts of PtCl2. The reaction is strongly accelerated when performed under an atmosphere of CO (1 atm). The resulting cyclobutenes are isolated in good to excellent yields for substrates bearing aliphatic as well as aromatic substituents R on their olefinic site. If the substituent R, however, is a very electron-rich arene, the cyclobutenes initially formed react further to give dimeric products with a previously unknown 1,2,2a,7a-tetrahydrospiro[cyclobuta[a]indene-7,1'-cyclobutane skeleton. A mechanism accounting for these experimental observations as well as for a deuterium-labeling experiment is proposed which implies reactive intermediates at the nonclassical cation/carbene interface. Furthermore it is shown that the PtCl2-catalyzed cyclobutene formation can be geared with subsequent ring-opening/ring-closing metathesis (ROM/RCM) events. Finally, a convenient "one pot" method for the preparation of the alkylidenecyclopropane substrates used in this study is presented, which is based on a modified Julia-Kocienski olefination of aldehydes with readily available 1-tert-butyl-1H-tetrazol-5-yl-cyclopropyl sulfone under Barbier conditions.
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Citations by publishers
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Wiley
96 publications, 49.48%
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American Chemical Society (ACS)
51 publications, 26.29%
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Springer Nature
1 publication, 0.52%
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Cellule MathDoc/CEDRAM
1 publication, 0.52%
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1 publication, 0.52%
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Autonomous Non-profit Organization Editorial Board of the journal Uspekhi Khimii
1 publication, 0.52%
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- We do not take into account publications without a DOI.
- Statistics recalculated only for publications connected to researchers, organizations and labs registered on the platform.
- Statistics recalculated weekly.
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Fürstner A., Aïssa C. PtCl2-Catalyzed Rearrangement of Methylenecyclopropanes // Journal of the American Chemical Society. 2006. Vol. 128. No. 19. pp. 6306-6307.
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Fürstner A., Aïssa C. PtCl2-Catalyzed Rearrangement of Methylenecyclopropanes // Journal of the American Chemical Society. 2006. Vol. 128. No. 19. pp. 6306-6307.
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TY - JOUR
DO - 10.1021/ja061392y
UR - https://doi.org/10.1021/ja061392y
TI - PtCl2-Catalyzed Rearrangement of Methylenecyclopropanes
T2 - Journal of the American Chemical Society
AU - Aïssa, Christophe
AU - Fürstner, Alois
PY - 2006
DA - 2006/04/26 00:00:00
PB - American Chemical Society (ACS)
SP - 6306-6307
IS - 19
VL - 128
SN - 0002-7863
SN - 1520-5126
ER -
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@article{2006_Fürstner,
author = {Christophe Aïssa and Alois Fürstner},
title = {PtCl2-Catalyzed Rearrangement of Methylenecyclopropanes},
journal = {Journal of the American Chemical Society},
year = {2006},
volume = {128},
publisher = {American Chemical Society (ACS)},
month = {apr},
url = {https://doi.org/10.1021/ja061392y},
number = {19},
pages = {6306--6307},
doi = {10.1021/ja061392y}
}
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Fürstner, Alois, and Christophe Aïssa. “PtCl2-Catalyzed Rearrangement of Methylenecyclopropanes.” Journal of the American Chemical Society, vol. 128, no. 19, Apr. 2006, pp. 6306-6307. https://doi.org/10.1021/ja061392y.