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

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)00000000000000000000000000000000111111110000000011111111000000000000000000000000P double bond characteristic in compounds 1-4. This paper provides the synthesis, structure, and bonding analysis of three halo-phosphinidenes and a bis-phosphinidene stabilized by a bicyclic (alkyl)(amino)carbene (BICAAC).

Automated summary

This study reports the synthesis and characterization of BICAAC-stabilized phosphinidenes. X-ray crystallography and NMR spectroscopy were used to characterize the compounds, and theoretical calculations indicated the presence of characteristic double bonds.