Template synthesis of 1,4,7-triphosphacyclononanes

Journal of the American Chemical Society
Peter G EdwardsPaul D Newman

Abstract

Iron(II) templates based on a [(eta(5)-Cp(R))Fe]+ core have been employed for the successful synthesis of 1,4,7-triphosphacyclononane derivatives (9-aneP3R'3) from a range of appropriately functionalized coordinated diphosphines and monophosphines. 1,2-Diphosphinoethane (1,2-dpe) or (2-phosphinoethyl)phenylphosphine (Phdpe) undergo a base-catalyzed Michael-type addition to trivinylphosphine, divinyl(benzyl)phosphine, or divinyl(phenyl)phosphine in [(eta(5)-Cp(R))Fe(diphosphine)(monophosphine)]+ complexes (2a-j) to give [(eta(5)-Cp(R))Fe(9aneP3R'3)]+ derivatives (4a-j) containing coordinated triphosphacyclononanes bearing one (with Phdpe) or two (with 1,2-dpe) secondary phosphine donors. The rates of macrocyclization show a dependence on the nature of the substituent(s) R on the cyclopentadienyl ligand with increased rates being observed along the series R = H5 < (Me3Si)H4 < 1,3-(Me3Si)2H3 approximately = Me5. For coupling reactions with trivinylphosphine, a pendant vinyl function remains in the macrocyclic product (4a-g) which is readily hydrogenated to the corresponding ethyl derivatives (5a-g). Further functionalization of coordinated secondary phosphines in the initially formed macrocycles (5a-g) is achieved by proton abstra...Continue Reading

References

Jan 6, 2006·Dalton Transactions : an International Journal of Inorganic Chemistry·Peter G EdwardsAndrew J Price

❮ Previous
Next ❯

Citations

Dec 11, 2008·Journal of the American Chemical Society·Oliver KaufholdF Ekkehardt Hahn
May 4, 2007·Chemical Communications : Chem Comm·Oliver KaufholdF Ekkehardt Hahn
Jun 30, 2009·Dalton Transactions : an International Journal of Inorganic Chemistry·Peter G EdwardsAndreas Stasch
Jul 24, 2010·Dalton Transactions : an International Journal of Inorganic Chemistry·Marco HartmannDavid Scheschkewitz
Aug 20, 2011·Dalton Transactions : an International Journal of Inorganic Chemistry·Thomas AlbersPaul D Newman
Jul 27, 2011·Dalton Transactions : an International Journal of Inorganic Chemistry·Peter G Edwards, F Ekkehardt Hahn
Apr 11, 2008·Dalton Transactions : an International Journal of Inorganic Chemistry·Huw A TallisAndreas Stasch
Apr 27, 2016·Dalton Transactions : an International Journal of Inorganic Chemistry·Katrina CoxPaul D Newman
Sep 6, 2014·Dalton Transactions : an International Journal of Inorganic Chemistry·Peter G EdwardsWenjian Zhang
Jan 6, 2009·Dalton Transactions : an International Journal of Inorganic Chemistry·A A KarasikO G Sinyashin
Nov 1, 2018·Dalton Transactions : an International Journal of Inorganic Chemistry·Lenali V WickramatungaPeter G Edwards
Sep 6, 2014·Dalton Transactions : an International Journal of Inorganic Chemistry·Peter G EdwardsCraig Williams
Jul 2, 2008·Inorganic Chemistry·Alexandre A MikhailineRobert H Morris

❮ Previous
Next ❯

Trending Feeds

COVID-19

Coronaviruses encompass a large family of viruses that cause the common cold as well as more serious diseases, such as the ongoing outbreak of coronavirus disease 2019 (COVID-19; formally known as 2019-nCoV). Coronaviruses can spread from animals to humans; symptoms include fever, cough, shortness of breath, and breathing difficulties; in more severe cases, infection can lead to death. This feed covers recent research on COVID-19.

Blastomycosis

Blastomycosis fungal infections spread through inhaling Blastomyces dermatitidis spores. Discover the latest research on blastomycosis fungal infections here.

Nuclear Pore Complex in ALS/FTD

Alterations in nucleocytoplasmic transport, controlled by the nuclear pore complex, may be involved in the pathomechanism underlying multiple neurodegenerative diseases including Amyotrophic Lateral Sclerosis and Frontotemporal Dementia. Here is the latest research on the nuclear pore complex in ALS and FTD.

Applications of Molecular Barcoding

The concept of molecular barcoding is that each original DNA or RNA molecule is attached to a unique sequence barcode. Sequence reads having different barcodes represent different original molecules, while sequence reads having the same barcode are results of PCR duplication from one original molecule. Discover the latest research on molecular barcoding here.

Chronic Fatigue Syndrome

Chronic fatigue syndrome is a disease characterized by unexplained disabling fatigue; the pathology of which is incompletely understood. Discover the latest research on chronic fatigue syndrome here.

Evolution of Pluripotency

Pluripotency refers to the ability of a cell to develop into three primary germ cell layers of the embryo. This feed focuses on the mechanisms that underlie the evolution of pluripotency. Here is the latest research.

Position Effect Variegation

Position Effect Variagation occurs when a gene is inactivated due to its positioning near heterochromatic regions within a chromosome. Discover the latest research on Position Effect Variagation here.

STING Receptor Agonists

Stimulator of IFN genes (STING) are a group of transmembrane proteins that are involved in the induction of type I interferon that is important in the innate immune response. The stimulation of STING has been an active area of research in the treatment of cancer and infectious diseases. Here is the latest research on STING receptor agonists.

Microbicide

Microbicides are products that can be applied to vaginal or rectal mucosal surfaces with the goal of preventing, or at least significantly reducing, the transmission of sexually transmitted infections. Here is the latest research on microbicides.