Isolation of a Staudinger‐type Intermediate Utilizing a Five‐Membered Phosphorus‐Centered Biradicaloid

Abstract: The Staudinger reaction provides chemists with a valuable tool for the reduction of azides, which are notoriously unstable and can decompose explosively. By providing a controlled method for the conversion of azides to amines, the reaction opened up new avenues for the synthesis of various amine‐containing compounds that are widely used in natural products, pharmaceuticals and polymers. The Staudinger reaction begins with the nucleophilic attack of a trivalent phosphine (usually triphenylphosphine), leading to the formation of a triazenide intermediate, a highly reactive species. Here we report how a divalent phosphorus‐centered biradicaloid reacts with covalent azides and show that it is possible to capture and fully characterize the transient intermediate. The experimental data is supported by quantum chemical calculations of the reaction paths and in terms of thermodynamics and chemical bonding.

Angaben zum Objekt

• Standort: Deutsche Nationalbibliothek Frankfurt am Main
• Umfang: Online-Ressource
• Sprache: Englisch

Verweise und Beziehungen

• Erschienen in: Isolation of a Staudinger‐type Intermediate Utilizing a Five‐Membered Phosphorus‐Centered Biradicaloid ; day:13 ; month:12 ; year:2024 ; extent:8 ; Chemistry - a European journal ; (13.12.2024) (gesamt 8)

Beteiligte, Orts- und Zeitangaben

• Urheber: Pilopp, Y. ; Bresien, Jonas ; Lüdtke, K. P. ; Schulz, Axel

Weitere Informationen

• DOI: 10.1002/chem.202403893
• URN: urn:nbn:de:101:1-2412141306209.450344950447
• Rechteinformation: Open Access; Der Zugriff auf das Objekt ist unbeschränkt möglich.
• Letzte Aktualisierung: 15.08.2025, 07:26 MESZ