Bicyclic (alkyl)(amino)carbene (BICAAC)-supported phosphinidenes

Abstract

Herein, the synthesis and characterization of bicyclic (alkyl)(amino)carbene (BICAAC)-stabilized phosphinidenes (1–4) are reported. Compounds 1–3 were obtained by reacting trihalophosphine [PX₃, X = Cl (1), Br (2), I (3)] with BICAAC in THF. A BICAAC-stabilized bis-phosphinidene (4) was obtained from the reduction of compound 2. All four compounds were characterized by X-ray crystallography and heteronuclear NMR spectroscopy. Theoretical calculations indicated the predominant C(carbene)P double bond characteristic in compounds 1–4.