112151-67-4Relevant academic research and scientific papers
Reactive E=C(p-p)? Systems, XIV. - Synthesis and Structure of Phosphaalkenes of the Type F3CP=C(F)NR2
Grobe, Joseph,Van, Duc Le,Nientiedt, Juergen,Krebs, Bernt,Dartmann, Mechthild
, p. 655 - 664 (2007/10/02)
Perfluoro-2-phosphapropene 1 reacts quantitatively with secondary amines R2NH in the molar ratio of 1:2 at temperatures between -120 and -40 deg C to give (trifluoromethyl)phosphaalkenes of the type F3CP=C(F)NR2 .Diphenylamine does not react in the same way even at room temperature.The same products are obtained by the reaction of (CF3)2PH with R2NH and R2NH/NEt3, respectively, in molar ratios of 1:3 or 1:1:2.The new compounds 4-9 just as 2 and 3 are stable at room temperature and without exception have Z configuration.The X-ray structure analysis of 1-(dimethylamino)-1,3,3,3-tetrafluoro-2-phospha-1-propene (2) proves the participation of the lone pair on nitrogen in stabilizing the system.The lattice of 2 contains C4H6F4NP molecules with an almost planar CP=C(F)NC2 skeleton.The PC bond distance amounts 1.744(2) Angstroem, the CN bond is 0.16 Angstroem shorter than CN single bonds in amines suggesting a bond order near 2.The reaction of 2 with Cr(CO)5-(THF) yields the complex Cr(CO)5 (10) with P-coordination.In the crystal structure of 10 the CN distance of the coordinated ligand is somewhat smaller (1.29 Angstroem) and the PC bond is considerably longer (1.80 Angstroem) than in 2.At 25 deg C 10 is slowly transformed to give 2 and the binuclear complex 2F3CP=C(F)NMe2 (11).
