Selective formation of dihydrofuran fused [60] fullerene derivatives by TEMPO mediated [3 + 2] cycloaddition of medium chain β-keto esters to C60
Authors
Jakšić, Jovana
Mitrović, Aleksandra D.

Tokić-Vujošević, Zorana
Milčić, Miloš K.

Maslak, Veselin

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In this study, β-keto esters as readily available bio-based building blocks were used to decorate the C60 sphere. Generally, cyclopropanated fullerene derivatives are obtained by the standard Bingel–Hirsch procedure. Herein, omitting the iodine from the reaction mixture and adding TEMPO afforded dihydrofuran fused C60 fullerene derivatives. The mechanism of the reaction shifted from nucleophilic aliphatic substitution to oxidative [3 + 2] cycloaddition via fullerenyl cations as an intermediate. This mechanism is proposed based on a series of control experiments with radical scavengers. Therefore, dihydrofuran-fused C60 derivatives were selectively obtained in good yields and their structures were established based on UV-Vis, IR, NMR spectroscopy and mass spectrometry. The electrochemical properties of the synthesized compounds were investigated by cyclic voltammetry. DFT calculations were performed in order to investigate the difference in stability, electronic properties and π-electro...n delocalization between methano and furano fullerenes.
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RSC Advances, 2021, 11, 47, 29426-29432Publisher:
- Royal Society of Chemistry
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- Supplementary material: https://cherry.chem.bg.ac.rs/handle/123456789/4717
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https://cherry.chem.bg.ac.rs/handle/123456789/4717
DOI: 10.1039/D1RA03944J
ISSN: 2046-2069
WoS: 000702237900028
Scopus: 2-s2.0-85116237014
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Hemijski fakultet / Faculty of ChemistryTY - JOUR AU - Jakšić, Jovana AU - Mitrović, Aleksandra D. AU - Tokić-Vujošević, Zorana AU - Milčić, Miloš K. AU - Maslak, Veselin PY - 2021 UR - https://cherry.chem.bg.ac.rs/handle/123456789/4714 AB - In this study, β-keto esters as readily available bio-based building blocks were used to decorate the C60 sphere. Generally, cyclopropanated fullerene derivatives are obtained by the standard Bingel–Hirsch procedure. Herein, omitting the iodine from the reaction mixture and adding TEMPO afforded dihydrofuran fused C60 fullerene derivatives. The mechanism of the reaction shifted from nucleophilic aliphatic substitution to oxidative [3 + 2] cycloaddition via fullerenyl cations as an intermediate. This mechanism is proposed based on a series of control experiments with radical scavengers. Therefore, dihydrofuran-fused C60 derivatives were selectively obtained in good yields and their structures were established based on UV-Vis, IR, NMR spectroscopy and mass spectrometry. The electrochemical properties of the synthesized compounds were investigated by cyclic voltammetry. DFT calculations were performed in order to investigate the difference in stability, electronic properties and π-electron delocalization between methano and furano fullerenes. PB - Royal Society of Chemistry T2 - RSC Advances T1 - Selective formation of dihydrofuran fused [60] fullerene derivatives by TEMPO mediated [3 + 2] cycloaddition of medium chain β-keto esters to C60 VL - 11 IS - 47 SP - 29426 EP - 29432 DO - 10.1039/D1RA03944J ER -
@article{ author = "Jakšić, Jovana and Mitrović, Aleksandra D. and Tokić-Vujošević, Zorana and Milčić, Miloš K. and Maslak, Veselin", year = "2021", abstract = "In this study, β-keto esters as readily available bio-based building blocks were used to decorate the C60 sphere. Generally, cyclopropanated fullerene derivatives are obtained by the standard Bingel–Hirsch procedure. Herein, omitting the iodine from the reaction mixture and adding TEMPO afforded dihydrofuran fused C60 fullerene derivatives. The mechanism of the reaction shifted from nucleophilic aliphatic substitution to oxidative [3 + 2] cycloaddition via fullerenyl cations as an intermediate. This mechanism is proposed based on a series of control experiments with radical scavengers. Therefore, dihydrofuran-fused C60 derivatives were selectively obtained in good yields and their structures were established based on UV-Vis, IR, NMR spectroscopy and mass spectrometry. The electrochemical properties of the synthesized compounds were investigated by cyclic voltammetry. DFT calculations were performed in order to investigate the difference in stability, electronic properties and π-electron delocalization between methano and furano fullerenes.", publisher = "Royal Society of Chemistry", journal = "RSC Advances", title = "Selective formation of dihydrofuran fused [60] fullerene derivatives by TEMPO mediated [3 + 2] cycloaddition of medium chain β-keto esters to C60", volume = "11", number = "47", pages = "29426-29432", doi = "10.1039/D1RA03944J" }
Jakšić, J., Mitrović, A. D., Tokić-Vujošević, Z., Milčić, M. K.,& Maslak, V.. (2021). Selective formation of dihydrofuran fused [60] fullerene derivatives by TEMPO mediated [3 + 2] cycloaddition of medium chain β-keto esters to C60. in RSC Advances Royal Society of Chemistry., 11(47), 29426-29432. https://doi.org/10.1039/D1RA03944J
Jakšić J, Mitrović AD, Tokić-Vujošević Z, Milčić MK, Maslak V. Selective formation of dihydrofuran fused [60] fullerene derivatives by TEMPO mediated [3 + 2] cycloaddition of medium chain β-keto esters to C60. in RSC Advances. 2021;11(47):29426-29432. doi:10.1039/D1RA03944J .
Jakšić, Jovana, Mitrović, Aleksandra D., Tokić-Vujošević, Zorana, Milčić, Miloš K., Maslak, Veselin, "Selective formation of dihydrofuran fused [60] fullerene derivatives by TEMPO mediated [3 + 2] cycloaddition of medium chain β-keto esters to C60" in RSC Advances, 11, no. 47 (2021):29426-29432, https://doi.org/10.1039/D1RA03944J . .