Open Access
International Journal of Molecular Sciences, volume 24, issue 1, pages 671
Ring-Opening Metathesis Polymerization and Related Olefin Metathesis Reactions in Benzotrifluoride as an Environmentally Advantageous Medium
Ervin Kovács
1
,
Bence Balterer
2, 3
,
Anh Duc Nguyen
1
,
Györgyi Szarka
1
,
Michael C Owen
4
,
Attila Domjan
2
,
Béla Iván
1
Publication type: Journal Article
Publication date: 2022-12-30
Quartile SCImago
Q1
Quartile WOS
Q1
Impact factor: 5.6
ISSN: 16616596, 14220067
Catalysis
Organic Chemistry
Inorganic Chemistry
Physical and Theoretical Chemistry
Computer Science Applications
Spectroscopy
Molecular Biology
General Medicine
Abstract
A tremendous number of solvents, either as liquids or vapors, contaminate the environment on a daily basis worldwide. Olefin metathesis, which has been widely used as high-yielding protocols for ring-opening metathesis polymerization (ROMP), ring-closing metathesis (RCM), and isomerization reactions, is typically performed in toxic and volatile solvents such as dichloromethane. In this study, the results of our systematic experiments with the Grubbs G1, G2, and Hoveyda-Grubbs HG2 catalysts proved that benzotrifluoride (BTF) can replace dichloromethane (DCM) in these reactions, providing high yields and similar or even higher reaction rates in certain cases. The ROMP of norbornene resulted not only in high yields but also in polynorbornenes with a high molecular weight at low catalyst loadings. Ring-closing metathesis (RCM) experiments proved that, with the exception of the G1 catalyst, RCM occurs with similar high efficiencies in BTF as in DCM. It was found that isomerization of (Z)-but-2-ene-1,4-diyl diacetate with the G2 and HG2 catalysts proceeds at significantly higher initial rates in BTF than in DCM, leading to rapid isomerization with high yields in a short time. Overall, BTF is a suitable solvent for olefin metathesis, such as polymer syntheses by ROMP and the ring-closing and isomerization reactions.
Top-30
Citations by journals
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Russian Chemical Reviews
1 publication, 100%
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Citations by publishers
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Autonomous Non-profit Organization Editorial Board of the journal Uspekhi Khimii
1 publication, 100%
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Kovács E. et al. Ring-Opening Metathesis Polymerization and Related Olefin Metathesis Reactions in Benzotrifluoride as an Environmentally Advantageous Medium // International Journal of Molecular Sciences. 2022. Vol. 24. No. 1. p. 671.
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Kovács E., Balterer B., Nguyen A. D., Szarka G., Owen M. C., Domjan A., Iván B. Ring-Opening Metathesis Polymerization and Related Olefin Metathesis Reactions in Benzotrifluoride as an Environmentally Advantageous Medium // International Journal of Molecular Sciences. 2022. Vol. 24. No. 1. p. 671.
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TY - JOUR
DO - 10.3390/ijms24010671
UR - https://doi.org/10.3390/ijms24010671
TI - Ring-Opening Metathesis Polymerization and Related Olefin Metathesis Reactions in Benzotrifluoride as an Environmentally Advantageous Medium
T2 - International Journal of Molecular Sciences
AU - Kovács, Ervin
AU - Balterer, Bence
AU - Nguyen, Anh Duc
AU - Szarka, Györgyi
AU - Owen, Michael C
AU - Domjan, Attila
AU - Iván, Béla
PY - 2022
DA - 2022/12/30 00:00:00
PB - Multidisciplinary Digital Publishing Institute (MDPI)
SP - 671
IS - 1
VL - 24
SN - 1661-6596
SN - 1422-0067
ER -
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@article{2022_Kovács,
author = {Ervin Kovács and Bence Balterer and Anh Duc Nguyen and Györgyi Szarka and Michael C Owen and Attila Domjan and Béla Iván},
title = {Ring-Opening Metathesis Polymerization and Related Olefin Metathesis Reactions in Benzotrifluoride as an Environmentally Advantageous Medium},
journal = {International Journal of Molecular Sciences},
year = {2022},
volume = {24},
publisher = {Multidisciplinary Digital Publishing Institute (MDPI)},
month = {dec},
url = {https://doi.org/10.3390/ijms24010671},
number = {1},
pages = {671},
doi = {10.3390/ijms24010671}
}
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Kovács, Ervin, et al. “Ring-Opening Metathesis Polymerization and Related Olefin Metathesis Reactions in Benzotrifluoride as an Environmentally Advantageous Medium.” International Journal of Molecular Sciences, vol. 24, no. 1, Dec. 2022, p. 671. https://doi.org/10.3390/ijms24010671.