Regioselective synthesis of chiral dimethyl-bis(ethylenedithio)tetrathiafulvalene sulfones
Enantiopure (R,R) and (S,S)-dimethyl-bis(ethylenedithio)tetrathiafulvalene monosulfones have been synthesized by the aerial oxidation of the chiral dithiolates generated from the propionitrile-protected precursors. Both enantiomers crystallize in the orthorhombic chiral space group P212121. They sho...
| Main Authors: | , |
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| Format: | Article |
| Language: | English |
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Beilstein-Institut
2015-07-01
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| Series: | Beilstein Journal of Organic Chemistry |
| Subjects: | |
| Online Access: | https://doi.org/10.3762/bjoc.11.124 |
| _version_ | 1818942747745189888 |
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| author | Flavia Pop Narcis Avarvari |
| author_facet | Flavia Pop Narcis Avarvari |
| author_sort | Flavia Pop |
| collection | DOAJ |
| description | Enantiopure (R,R) and (S,S)-dimethyl-bis(ethylenedithio)tetrathiafulvalene monosulfones have been synthesized by the aerial oxidation of the chiral dithiolates generated from the propionitrile-protected precursors. Both enantiomers crystallize in the orthorhombic chiral space group P212121. They show a boat-type conformation of the TTF moiety, a rather rigid dithiin sulfone ring and the methyl groups in a bisequatorial conformation. Cyclic voltammetry measurements indicate fully reversible oxidation in radical cation and dication species. |
| first_indexed | 2024-12-20T07:16:21Z |
| format | Article |
| id | doaj.art-e5b2b5819a914d4db273ea416e73ac6f |
| institution | Directory Open Access Journal |
| issn | 1860-5397 |
| language | English |
| last_indexed | 2024-12-20T07:16:21Z |
| publishDate | 2015-07-01 |
| publisher | Beilstein-Institut |
| record_format | Article |
| series | Beilstein Journal of Organic Chemistry |
| spelling | doaj.art-e5b2b5819a914d4db273ea416e73ac6f2022-12-21T19:48:47ZengBeilstein-InstitutBeilstein Journal of Organic Chemistry1860-53972015-07-011111105111110.3762/bjoc.11.1241860-5397-11-124Regioselective synthesis of chiral dimethyl-bis(ethylenedithio)tetrathiafulvalene sulfonesFlavia Pop0Narcis Avarvari1Université d'Angers, CNRS, Laboratoire MOLTECH-Anjou, UMR 6200, UFR Sciences, Bât. K, 2 Bd. Lavoisier, 49045 Angers, FranceUniversité d'Angers, CNRS, Laboratoire MOLTECH-Anjou, UMR 6200, UFR Sciences, Bât. K, 2 Bd. Lavoisier, 49045 Angers, FranceEnantiopure (R,R) and (S,S)-dimethyl-bis(ethylenedithio)tetrathiafulvalene monosulfones have been synthesized by the aerial oxidation of the chiral dithiolates generated from the propionitrile-protected precursors. Both enantiomers crystallize in the orthorhombic chiral space group P212121. They show a boat-type conformation of the TTF moiety, a rather rigid dithiin sulfone ring and the methyl groups in a bisequatorial conformation. Cyclic voltammetry measurements indicate fully reversible oxidation in radical cation and dication species.https://doi.org/10.3762/bjoc.11.124chiralitycrystal structuresmolecular materialssulfonestetrathiafulvalenes |
| spellingShingle | Flavia Pop Narcis Avarvari Regioselective synthesis of chiral dimethyl-bis(ethylenedithio)tetrathiafulvalene sulfones Beilstein Journal of Organic Chemistry chirality crystal structures molecular materials sulfones tetrathiafulvalenes |
| title | Regioselective synthesis of chiral dimethyl-bis(ethylenedithio)tetrathiafulvalene sulfones |
| title_full | Regioselective synthesis of chiral dimethyl-bis(ethylenedithio)tetrathiafulvalene sulfones |
| title_fullStr | Regioselective synthesis of chiral dimethyl-bis(ethylenedithio)tetrathiafulvalene sulfones |
| title_full_unstemmed | Regioselective synthesis of chiral dimethyl-bis(ethylenedithio)tetrathiafulvalene sulfones |
| title_short | Regioselective synthesis of chiral dimethyl-bis(ethylenedithio)tetrathiafulvalene sulfones |
| title_sort | regioselective synthesis of chiral dimethyl bis ethylenedithio tetrathiafulvalene sulfones |
| topic | chirality crystal structures molecular materials sulfones tetrathiafulvalenes |
| url | https://doi.org/10.3762/bjoc.11.124 |
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