Synthesis and electrochemical properties of 3,4,5-tris(chlorophenyl)-1,2-diphosphaferrocenes
A novel representative of sodium 3,4,5-triaryl-1,2-diphosphacyclopentadienide containing a chloro substituent in the meta-position of the aryl groups was obtained with a high yield based on the reaction of tributyl(1,2,3-triarylcyclopropenyl)phosphonium bromide and sodium polyphosphides. Further rea...
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| Format: | Article |
| Language: | English |
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Beilstein-Institut
2022-09-01
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| Series: | Beilstein Journal of Organic Chemistry |
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| Online Access: | https://doi.org/10.3762/bjoc.18.139 |
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| author | Almaz A. Zagidullin Farida F. Akhmatkhanova Mikhail N. Khrizanforov Robert R. Fayzullin Tatiana P. Gerasimova Ilya A. Bezkishko Vasili A. Miluykov |
| author_facet | Almaz A. Zagidullin Farida F. Akhmatkhanova Mikhail N. Khrizanforov Robert R. Fayzullin Tatiana P. Gerasimova Ilya A. Bezkishko Vasili A. Miluykov |
| author_sort | Almaz A. Zagidullin |
| collection | DOAJ |
| description | A novel representative of sodium 3,4,5-triaryl-1,2-diphosphacyclopentadienide containing a chloro substituent in the meta-position of the aryl groups was obtained with a high yield based on the reaction of tributyl(1,2,3-triarylcyclopropenyl)phosphonium bromide and sodium polyphosphides. Further reaction of sodium 3,4,5-tris(3-chlorophenyl)-1,2-diphosphacyclopentadienide with [FeCp(η6-C6H5CH3)][PF6] complex gives a new 3,4,5-tris(3-chlorophenyl)-1,2-diphosphaferrocene. The electrochemical properties of 3,4,5-tris(3-chlorophenyl)-1,2-diphosphaferrocene were studied and compared to 3,4,5-tris(4-chlorophenyl)-1,2-diphosphaferrocene. It was found that the position of the chlorine atom on the aryl fragment has an influence on the reduction potential of 1,2-diphosphaferrocenes, while the oxidation potentials do not change. |
| first_indexed | 2024-04-12T03:23:23Z |
| format | Article |
| id | doaj.art-de3a41e2351e47508c84be93bd4be863 |
| institution | Directory Open Access Journal |
| issn | 1860-5397 |
| language | English |
| last_indexed | 2024-04-12T03:23:23Z |
| publishDate | 2022-09-01 |
| publisher | Beilstein-Institut |
| record_format | Article |
| series | Beilstein Journal of Organic Chemistry |
| spelling | doaj.art-de3a41e2351e47508c84be93bd4be8632022-12-22T03:49:48ZengBeilstein-InstitutBeilstein Journal of Organic Chemistry1860-53972022-09-011811338134510.3762/bjoc.18.1391860-5397-18-139Synthesis and electrochemical properties of 3,4,5-tris(chlorophenyl)-1,2-diphosphaferrocenesAlmaz A. Zagidullin0Farida F. Akhmatkhanova1Mikhail N. Khrizanforov2Robert R. Fayzullin3Tatiana P. Gerasimova4Ilya A. Bezkishko5Vasili A. Miluykov6Arbuzov Institute of Organic and Physical Chemistry, FRC Kazan Scientific Center, Russian Academy of Sciences, 8 Arbuzov Street, 420088 Kazan, Russian Federation Arbuzov Institute of Organic and Physical Chemistry, FRC Kazan Scientific Center, Russian Academy of Sciences, 8 Arbuzov Street, 420088 Kazan, Russian Federation Arbuzov Institute of Organic and Physical Chemistry, FRC Kazan Scientific Center, Russian Academy of Sciences, 8 Arbuzov Street, 420088 Kazan, Russian Federation Arbuzov Institute of Organic and Physical Chemistry, FRC Kazan Scientific Center, Russian Academy of Sciences, 8 Arbuzov Street, 420088 Kazan, Russian Federation Arbuzov Institute of Organic and Physical Chemistry, FRC Kazan Scientific Center, Russian Academy of Sciences, 8 Arbuzov Street, 420088 Kazan, Russian Federation Arbuzov Institute of Organic and Physical Chemistry, FRC Kazan Scientific Center, Russian Academy of Sciences, 8 Arbuzov Street, 420088 Kazan, Russian Federation Arbuzov Institute of Organic and Physical Chemistry, FRC Kazan Scientific Center, Russian Academy of Sciences, 8 Arbuzov Street, 420088 Kazan, Russian Federation A novel representative of sodium 3,4,5-triaryl-1,2-diphosphacyclopentadienide containing a chloro substituent in the meta-position of the aryl groups was obtained with a high yield based on the reaction of tributyl(1,2,3-triarylcyclopropenyl)phosphonium bromide and sodium polyphosphides. Further reaction of sodium 3,4,5-tris(3-chlorophenyl)-1,2-diphosphacyclopentadienide with [FeCp(η6-C6H5CH3)][PF6] complex gives a new 3,4,5-tris(3-chlorophenyl)-1,2-diphosphaferrocene. The electrochemical properties of 3,4,5-tris(3-chlorophenyl)-1,2-diphosphaferrocene were studied and compared to 3,4,5-tris(4-chlorophenyl)-1,2-diphosphaferrocene. It was found that the position of the chlorine atom on the aryl fragment has an influence on the reduction potential of 1,2-diphosphaferrocenes, while the oxidation potentials do not change.https://doi.org/10.3762/bjoc.18.139cyclopropenyl bromideelectrochemical propertiesphosphacyclopentadienide anionphosphaferrocenephosphonium saltphosphorus heterocycle |
| spellingShingle | Almaz A. Zagidullin Farida F. Akhmatkhanova Mikhail N. Khrizanforov Robert R. Fayzullin Tatiana P. Gerasimova Ilya A. Bezkishko Vasili A. Miluykov Synthesis and electrochemical properties of 3,4,5-tris(chlorophenyl)-1,2-diphosphaferrocenes Beilstein Journal of Organic Chemistry cyclopropenyl bromide electrochemical properties phosphacyclopentadienide anion phosphaferrocene phosphonium salt phosphorus heterocycle |
| title | Synthesis and electrochemical properties of 3,4,5-tris(chlorophenyl)-1,2-diphosphaferrocenes |
| title_full | Synthesis and electrochemical properties of 3,4,5-tris(chlorophenyl)-1,2-diphosphaferrocenes |
| title_fullStr | Synthesis and electrochemical properties of 3,4,5-tris(chlorophenyl)-1,2-diphosphaferrocenes |
| title_full_unstemmed | Synthesis and electrochemical properties of 3,4,5-tris(chlorophenyl)-1,2-diphosphaferrocenes |
| title_short | Synthesis and electrochemical properties of 3,4,5-tris(chlorophenyl)-1,2-diphosphaferrocenes |
| title_sort | synthesis and electrochemical properties of 3 4 5 tris chlorophenyl 1 2 diphosphaferrocenes |
| topic | cyclopropenyl bromide electrochemical properties phosphacyclopentadienide anion phosphaferrocene phosphonium salt phosphorus heterocycle |
| url | https://doi.org/10.3762/bjoc.18.139 |
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