Article Dans Une Revue Journal of the American Chemical Society Année : 2025

A Crystalline Annelated Pyridin-1-ylidene and Its Isomerization into a Pyridin-3-ylidene

Jakub Talcik
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Résumé

An isolable ring-fused pyridinylidene (a so-called Hammick intermediate) was synthesized from a benzo[h]isoquinolinium salt, and its structure in the solid state was determined. The isolation of this first-of-its-kind pyridine-derived aromatic N-heterocyclic carbene was made possible due to the presence of an adamantyl group on nitrogen, forcing the nitrogen to be planar and enhancing both π-donation and steric protection, and to its unique polycyclic structure, which displays an intramolecular C-H···Ccarbene interaction. Additionally, an example of isomerization of a carbene into another carbene, namely, a benzo[h]isoquinolin-1-ylidene into a benzo[h]isoquinolin-3-ylidene, is reported.

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hal-05093465 , version 1 (21-07-2025)

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Jan Lorkowski, Levan Gojiashvili, Patrick Yorkgitis, Delphine Pichon, Jakub Talcik, et al.. A Crystalline Annelated Pyridin-1-ylidene and Its Isomerization into a Pyridin-3-ylidene. Journal of the American Chemical Society, 2025, 147 (18), pp.14972-14977. ⟨10.1021/jacs.5c05642⟩. ⟨hal-05093465⟩
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