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3,4,5-三(氯苯基)-1,2-二磷杂二茂铁的合成与电化学性质

Synthesis and electrochemical properties of 3,4,5-tris(chlorophenyl)-1,2-diphosphaferrocenes.

作者信息

Zagidullin Almaz A, Akhmatkhanova Farida F, Khrizanforov Mikhail N, Fayzullin Robert R, Gerasimova Tatiana P, Bezkishko Ilya A, Miluykov Vasili A

机构信息

Arbuzov Institute of Organic and Physical Chemistry, FRC Kazan Scientific Center, Russian Academy of Sciences, 8 Arbuzov Street, 420088 Kazan, Russian Federation.

出版信息

Beilstein J Org Chem. 2022 Sep 27;18:1338-1345. doi: 10.3762/bjoc.18.139. eCollection 2022.

DOI:10.3762/bjoc.18.139
PMID:36247980
原文链接:https://pmc.ncbi.nlm.nih.gov/articles/PMC9531555/
Abstract

A novel representative of sodium 3,4,5-triaryl-1,2-diphosphacyclopentadienide containing a chloro substituent in the -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(η-CHCH)][PF] 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.

摘要

基于三丁基(1,2,3-三芳基环丙烯基)溴化鏻与多硫化钠的反应,高产率地得到了一种新型的3,4,5-三芳基-1,2-二磷杂环戊二烯钠衍生物,其芳基的α位含有氯取代基。3,4,5-三(3-氯苯基)-1,2-二磷杂环戊二烯钠与[FeCp(η-C₂H₄)][PF₆]配合物进一步反应得到一种新的3,4,5-三(3-氯苯基)-1,2-二磷杂二茂铁。研究了3,4,5-三(3-氯苯基)-1,2-二磷杂二茂铁的电化学性质,并与3,4,5-三(4-氯苯基)-1,2-二磷杂二茂铁进行了比较。结果发现,芳基片段上氯原子的位置对1,2-二磷杂二茂铁的还原电位有影响,而氧化电位不变。

https://cdn.ncbi.nlm.nih.gov/pmc/blobs/ae74/9531555/1470abaa8166/Beilstein_J_Org_Chem-18-1338-g006.jpg
https://cdn.ncbi.nlm.nih.gov/pmc/blobs/ae74/9531555/615b5f565074/Beilstein_J_Org_Chem-18-1338-g007.jpg
https://cdn.ncbi.nlm.nih.gov/pmc/blobs/ae74/9531555/a64e53a0ff14/Beilstein_J_Org_Chem-18-1338-g008.jpg
https://cdn.ncbi.nlm.nih.gov/pmc/blobs/ae74/9531555/e5336edf3888/Beilstein_J_Org_Chem-18-1338-g002.jpg
https://cdn.ncbi.nlm.nih.gov/pmc/blobs/ae74/9531555/f2dd22672cd2/Beilstein_J_Org_Chem-18-1338-g009.jpg
https://cdn.ncbi.nlm.nih.gov/pmc/blobs/ae74/9531555/019a2b1e2bcb/Beilstein_J_Org_Chem-18-1338-g003.jpg
https://cdn.ncbi.nlm.nih.gov/pmc/blobs/ae74/9531555/c8926bfa0b55/Beilstein_J_Org_Chem-18-1338-g004.jpg
https://cdn.ncbi.nlm.nih.gov/pmc/blobs/ae74/9531555/0fc63ea30871/Beilstein_J_Org_Chem-18-1338-g005.jpg
https://cdn.ncbi.nlm.nih.gov/pmc/blobs/ae74/9531555/1470abaa8166/Beilstein_J_Org_Chem-18-1338-g006.jpg
https://cdn.ncbi.nlm.nih.gov/pmc/blobs/ae74/9531555/615b5f565074/Beilstein_J_Org_Chem-18-1338-g007.jpg
https://cdn.ncbi.nlm.nih.gov/pmc/blobs/ae74/9531555/a64e53a0ff14/Beilstein_J_Org_Chem-18-1338-g008.jpg
https://cdn.ncbi.nlm.nih.gov/pmc/blobs/ae74/9531555/e5336edf3888/Beilstein_J_Org_Chem-18-1338-g002.jpg
https://cdn.ncbi.nlm.nih.gov/pmc/blobs/ae74/9531555/f2dd22672cd2/Beilstein_J_Org_Chem-18-1338-g009.jpg
https://cdn.ncbi.nlm.nih.gov/pmc/blobs/ae74/9531555/019a2b1e2bcb/Beilstein_J_Org_Chem-18-1338-g003.jpg
https://cdn.ncbi.nlm.nih.gov/pmc/blobs/ae74/9531555/c8926bfa0b55/Beilstein_J_Org_Chem-18-1338-g004.jpg
https://cdn.ncbi.nlm.nih.gov/pmc/blobs/ae74/9531555/0fc63ea30871/Beilstein_J_Org_Chem-18-1338-g005.jpg
https://cdn.ncbi.nlm.nih.gov/pmc/blobs/ae74/9531555/1470abaa8166/Beilstein_J_Org_Chem-18-1338-g006.jpg

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