Synthesis and Characterization of (Disilylanilino)Phosphines

GRAPHICAL ABSTRACT

The disilyl(4-bromo)aniline (Me₃Si)₂NC₆H₄Br (A) readily undergoes metal-halogen exchange to give the reactive organolithium derivative (Me₃Si)₂NC₆H₄Li (B). Subsequent reactions with various chlorophosphines, R(R′)PCl, or chloro(disilylamino)phosphines, (Me₃Si)₂NP(R)Cl, were used to prepare three varieties of the title compounds: (Me₃Si)₂NC₆H₄P(R′)R (1: R = R′ = NMe₂; 2: R = R′ = OCH₂CF₃; 3: R = Ph, R′ = OCH₂CF₃; 4: R = R′ = Ph; 5: R = Ph, R′ = Me), (Me₃Si)₂NC₆H₄P(R)N(SiMe₃)₂ [6: R = Me; 7: R = i-Pr; 8: R = n-Bu, 9: R = OCH₂CF₃; 10: R = C₆H₄N(SiMe₃)₂; 11: R = Ph], and (Me₃Si)₂NC₆H₄P(Ph)R [12: R = n-Bu; 13: R = C₆H₄N(SiMe₃)₂]. The new compounds 1–13 were generally obtained as colorless, distillable liquids that were fully characterized by NMR (¹H, ¹³C, and ³¹P) spectroscopy and elemental analysis.

Keywords:

• Silylaniline
• anilinophosphine
• phosphine
• aminophosphine
• silylamine