ArticleChemistry (Weinheim an der Bergstrasse, Germany)2025
Isolation of a Staudinger-type Intermediate Utilizing a Five-Membered Phosphorus-Centered Biradicaloid.
Article in Chemistry (Weinheim an der Bergstrasse, Germany), 2025. The graph could read no effect estimate from its abstract, so it casts no vote on the map. Cited by 3 papers.
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3 citing papers in PubMed.
- The Staudinger reaction: a versatile synthetic tool for the construction of β-lactams, heterocycles, and functional organic molecules.RSC advances · 2026Review
- Büchner-type ring expansion of aromatic main-group biradicaloids toward phosphorus radical-derived NIR-II photothermal materials.Chemical science · 2025Article
- Isolation of a Staudinger-type Intermediate Utilizing a Five-Membered Phosphorus-Centered Biradicaloid.Chemistry (Weinheim an der Bergstrasse, Germany) · 2025Article
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4 authors.
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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.
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