Structure and Mechanism Revision of a Catalyzed Cyclization of Benzaldehyde Bearing Alkyne-Nitrile

P. Šafář (1) , Š. Marchalín (1) , M. Šoral (1) , J. Moncol (1) , Adam Daïch (2, 3)

1 Slovak University of Technology in Bratislava
2 URCOM - Unité de Recherche en Chimie Organique et Macromoléculaire
3 INC3M - Institut Normand de Chimie Moléculaire Médicinale et Macromoléculaire

Pt(II)-catalyzed carbocyclization of benzaldehyde containing a keto-nitrile functionality resulted in the formation, respectively, of isochromenes and spiro-lactones instead of fused lactams and spiro-lactams as was previously reported. The reaction mechanism was proposed, and the products were identified by multidimensional NMR, IR, and X-ray analysis. The structure of these new products was also confirmed by their synthesis in an unambiguous manner using practical and short approaches. © 2017 American Chemical Society.

Keywords: Crystal structure; Cyclization; Amides; Ketones; Chemical structure

Domains: Chemical Sciences

P. Šafář, Š. Marchalín, M. Šoral, J. Moncol, Adam Daïch. Structure and Mechanism Revision of a Catalyzed Cyclization of Benzaldehyde Bearing Alkyne-Nitrile. Organic Letters, 2017, 19 (18), pp.4742-4745. ⟨10.1021/acs.orglett.7b01881⟩. ⟨hal-02413277⟩