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Unveiling the Phosphine-Mediated -Transfer from Azide to Isocyanide en Route to Carbodiimides and 4-Imino-1,3,2-diazaphosphetidines.
Org Lett
January 2025
Departamento de Química Orgánica, Facultad de Química, Regional Campus of International Excellence "Campus Mare Nostrum", Universidad de Murcia, E-30100Murcia, Spain.
Intramolecular reactions between isocyano and iminophosphorane functions yield species containing an embedded 1,3,2-diazaphosphetidine ring, as result of the [2 + 2] cycloaddition of the primary reactive product, the cyclic carbodiimide, with a second unit of reactant. DFT studies reveal a first rate-determining step entailing a [2 + 1] cycloaddition involving the isocyanide carbon atom and the P═N double bond, with the further intervention of a dipolar precursor of the intermediate carbodiimide. The 1,3,2-diazaphosphetidine ring of the final products is shown to be hydrolytically and thermally labile.
View Article and Find Full Text PDFElectrosynthesis of iminophosphoranes and applications in nickel catalysis.
Chem Sci
April 2024
Analytical Research and Development, Merck & Co., Inc. Rahway New Jersey 07065 USA.
P(v) iminophosphorane compounds are accessed electrochemical oxidation of commercially available P(iii) phosphines, including mono-, di- and tri-dentate phosphines, as well as chiral phosphines. The reaction uses inexpensive bis(trimethylsilyl)carbodiimide as an efficient and safe aminating reagent. DFT calculations, cyclic voltammetry, and NMR studies provide insight into the reaction mechanism.
View Article and Find Full Text PDFIntroducing -Heterocyclic Iminophosphoranes (NHIPs): Synthesis by [3 + 2] Cycloaddition of Azophosphines with Alkynes and Reactivity Studies.
Inorg Chem
September 2022
Department of Chemistry, Massachusetts Institute of Technology, Cambridge, Massachusetts 02139, United States.
Article Synopsis
- Azophosphines were synthesized using -aryl-(trimethylsilyl)diazenes and RPCl, leading to new compounds called heterocyclic iminophosphoranes (NHIPs) that resemble cyclic carbenes and are versatile in their chemical compatibility.
- NHIPs showed a range of basicity values in acetonitrile, with some having σ-donor strengths similar to known reagents, indicating strong electron-donating properties, and reacted easily with different substances to yield interesting chemical structures.
- The research highlights the potential applications of NHIPs in synthetic chemistry due to their easy synthesis, adjustable properties, and ability to stabilize reactive species, aiming for future uses in various chemical
A cyclic divalent N(I) species isoelectronic to carbodiphosphoranes.
Chem Commun (Camb)
May 2022
Institut de Chimie Moléculaire et des Matériaux d'Orsay, CNRS UMR 8182, Université Paris-Saclay, Bâtiment 420, 91405 Orsay cedex, France.
The formation of a rare type of diphosphazenium cation is described. Its synthesis features a unique oxidative dealkylation of an iminophosphorane-phosphole by a silver(I) salt. DFT study of this compound reveals the low valent character of the N(I) center.
View Article and Find Full Text PDFFe and Fe Phosphasalen Complexes: Synthesis, Characterization, and Catalytic Application for 2-Naphthol Oxidative Coupling.
Chemistry
October 2020
Laboratoire de Chimie Moléculaire, CNRS UMR 9168, École Polytechnique, Institut Polytechnique de Paris, 91128, Palaiseau, France.
We report on the synthesis and characterization of three iron(III) phosphasalen complexes, [Fe (Psalen)(X)] differing in the nature of the counter-anion/exogenous ligand (X =Cl , NO , OTf ), as well as the neutral iron(II) analogue, [Fe (Psalen)]. Phosphasalen (Psalen) differs from salen by the presence of iminophosphorane (P=N) functions in place of the imines. All the complexes were characterized by single-crystal X-ray diffraction, UV/Vis, EPR, and cyclic voltammetry.
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