Synthesis and characterization of original fluorinated bis-cyclic carbonates and xanthates from a fluorinated epoxide
The development of efficient methods for the cycloaddition of CX2 (carbon dioxide (X${=}$O) or carbon disulfide (X${=}$S)) with fluorinated epoxides to produce five-membered cyclic carbonates (CCs) or cyclic xanthates (XAs) is a very attractive topic. In this work, the cycloaddition of CX2 with hexa...
Saved in:
| Main Authors: | , , , , , |
|---|---|
| Format: | Article |
| Language: | English |
| Published: |
Académie des sciences
2023-02-01
|
| Series: | Comptes Rendus. Chimie |
| Subjects: | |
| Online Access: | https://comptes-rendus.academie-sciences.fr/chimie/articles/10.5802/crchim.216/ |
| Tags: |
Add Tag
No Tags, Be the first to tag this record!
|
| _version_ | 1825206117977817088 |
|---|---|
| author | Alaaeddine, Ali Ladmiral, Vincent El Malti, Wassim Haydar, Lolwa Caillol, Sylvain Améduri, Bruno |
| author_facet | Alaaeddine, Ali Ladmiral, Vincent El Malti, Wassim Haydar, Lolwa Caillol, Sylvain Améduri, Bruno |
| author_sort | Alaaeddine, Ali |
| collection | DOAJ |
| description | The development of efficient methods for the cycloaddition of CX2 (carbon dioxide (X${=}$O) or carbon disulfide (X${=}$S)) with fluorinated epoxides to produce five-membered cyclic carbonates (CCs) or cyclic xanthates (XAs) is a very attractive topic. In this work, the cycloaddition of CX2 with hexafluoropropene oxide (HFPO) was performed in the presence of a lithium bromide (LiBr) catalyst and optimized in terms of temperature, solvent, pressure, and reaction time. Then, the optimized conditions were tried in the cycloaddition of CX2 with 2-(trifluoromethyl)oxirane (TFEO) for reproducibility, leading to the corresponding products in high yields. Finally, two original fluorinated five-membered bis-CCs and bis-XAs were synthesized in high yields (85 and 87%) by reacting CX2 with 1,4-bis($2^{\prime }{,}3^{\prime }$-epoxypropyl) perfluorobutane (BEPFB). All of the resulting compounds were characterized by FTIR, 1H, 19F, and 13C NMR spectroscopy. |
| format | Article |
| id | doaj-art-ddeb70fe34b9403db01293f6ed894fa5 |
| institution | Kabale University |
| issn | 1878-1543 |
| language | English |
| publishDate | 2023-02-01 |
| publisher | Académie des sciences |
| record_format | Article |
| series | Comptes Rendus. Chimie |
| spelling | doaj-art-ddeb70fe34b9403db01293f6ed894fa52025-02-07T13:38:00ZengAcadémie des sciencesComptes Rendus. Chimie1878-15432023-02-0126G1192810.5802/crchim.21610.5802/crchim.216Synthesis and characterization of original fluorinated bis-cyclic carbonates and xanthates from a fluorinated epoxideAlaaeddine, Ali0Ladmiral, Vincent1https://orcid.org/0000-0002-7590-4800El Malti, Wassim2https://orcid.org/0000-0003-0212-3939Haydar, Lolwa3Caillol, Sylvain4https://orcid.org/0000-0003-3106-5547Améduri, Bruno5https://orcid.org/0000-0003-4217-6664ICGM, Univ Montpellier, CNRS, ENSCM, Montpellier, FranceICGM, Univ Montpellier, CNRS, ENSCM, Montpellier, FranceCollege of Engineering and Technology, American University of the Middle East, KuwaitICGM, Univ Montpellier, CNRS, ENSCM, Montpellier, FranceICGM, Univ Montpellier, CNRS, ENSCM, Montpellier, FranceICGM, Univ Montpellier, CNRS, ENSCM, Montpellier, FranceThe development of efficient methods for the cycloaddition of CX2 (carbon dioxide (X${=}$O) or carbon disulfide (X${=}$S)) with fluorinated epoxides to produce five-membered cyclic carbonates (CCs) or cyclic xanthates (XAs) is a very attractive topic. In this work, the cycloaddition of CX2 with hexafluoropropene oxide (HFPO) was performed in the presence of a lithium bromide (LiBr) catalyst and optimized in terms of temperature, solvent, pressure, and reaction time. Then, the optimized conditions were tried in the cycloaddition of CX2 with 2-(trifluoromethyl)oxirane (TFEO) for reproducibility, leading to the corresponding products in high yields. Finally, two original fluorinated five-membered bis-CCs and bis-XAs were synthesized in high yields (85 and 87%) by reacting CX2 with 1,4-bis($2^{\prime }{,}3^{\prime }$-epoxypropyl) perfluorobutane (BEPFB). All of the resulting compounds were characterized by FTIR, 1H, 19F, and 13C NMR spectroscopy.https://comptes-rendus.academie-sciences.fr/chimie/articles/10.5802/crchim.216/Carbon dioxide (CO<sub>2</sub>)Carbon disulfide (CS<sub>2</sub>)CycloadditionCyclic carbonatesCyclic xanthatesFluorinated epoxidesRenewable carbon source |
| spellingShingle | Alaaeddine, Ali Ladmiral, Vincent El Malti, Wassim Haydar, Lolwa Caillol, Sylvain Améduri, Bruno Synthesis and characterization of original fluorinated bis-cyclic carbonates and xanthates from a fluorinated epoxide Comptes Rendus. Chimie Carbon dioxide (CO<sub>2</sub>) Carbon disulfide (CS<sub>2</sub>) Cycloaddition Cyclic carbonates Cyclic xanthates Fluorinated epoxides Renewable carbon source |
| title | Synthesis and characterization of original fluorinated bis-cyclic carbonates and xanthates from a fluorinated epoxide |
| title_full | Synthesis and characterization of original fluorinated bis-cyclic carbonates and xanthates from a fluorinated epoxide |
| title_fullStr | Synthesis and characterization of original fluorinated bis-cyclic carbonates and xanthates from a fluorinated epoxide |
| title_full_unstemmed | Synthesis and characterization of original fluorinated bis-cyclic carbonates and xanthates from a fluorinated epoxide |
| title_short | Synthesis and characterization of original fluorinated bis-cyclic carbonates and xanthates from a fluorinated epoxide |
| title_sort | synthesis and characterization of original fluorinated bis cyclic carbonates and xanthates from a fluorinated epoxide |
| topic | Carbon dioxide (CO<sub>2</sub>) Carbon disulfide (CS<sub>2</sub>) Cycloaddition Cyclic carbonates Cyclic xanthates Fluorinated epoxides Renewable carbon source |
| url | https://comptes-rendus.academie-sciences.fr/chimie/articles/10.5802/crchim.216/ |
| work_keys_str_mv | AT alaaeddineali synthesisandcharacterizationoforiginalfluorinatedbiscycliccarbonatesandxanthatesfromafluorinatedepoxide AT ladmiralvincent synthesisandcharacterizationoforiginalfluorinatedbiscycliccarbonatesandxanthatesfromafluorinatedepoxide AT elmaltiwassim synthesisandcharacterizationoforiginalfluorinatedbiscycliccarbonatesandxanthatesfromafluorinatedepoxide AT haydarlolwa synthesisandcharacterizationoforiginalfluorinatedbiscycliccarbonatesandxanthatesfromafluorinatedepoxide AT caillolsylvain synthesisandcharacterizationoforiginalfluorinatedbiscycliccarbonatesandxanthatesfromafluorinatedepoxide AT ameduribruno synthesisandcharacterizationoforiginalfluorinatedbiscycliccarbonatesandxanthatesfromafluorinatedepoxide |