393-02-2Relevant academic research and scientific papers
Reactive E=C(p-p)?-Systems, XXVIII. Synthesis and Reactivity of the Iminomethylenephosphane F3C-P=C=N-tBu
Grobe, Joseph,Van, Duc Le,Grosspietsch, Thomas
, p. 978 - 984 (2007/10/02)
Iminomethylenephosphanes, Fluorophosphaalkenes, Bis(trifluormethyl)phosphane, Chiral Aminophosphanes The reaction of perfluoro-2-phosphapropene F3CP=CF2 (1) with tert-butylamine or isopropylamine in a 1:3 molar ratio leads to the novel iminomethylene phosphanes F3CP=C=N(tBu) and F3CP=C=N(iPr) , respectively. 2 slowly decomposes at room temperature giving tert-butylisonitrile and the cyclophosphanes (F3CP)n (n = 3,4,5). 3 is found to be less stable than 2 and for example is attacked by primary amines.The reaction of 2 with 2,3-dimethyl-1,3-butadiene or trimethylphosphane yields, on the one hand, the cycloaddition product of bis(trifluormethyl)diphosphene (4), and on the other hand, the phosphorus ylid Me3P=PCF3 (5) together with (tBu)NC. 2 and 3, respectively, are not obtained from (F3C)2PH and the corresponding primary amines in a series of HF elimination and H2NR addition reactions.The main products formed from a 1:4 molar mixture of (F3C)2PH and H2N(iPr) in a one-pot procedure were shown to be the chiral phosphanes F3CPCH (6), F3CPCHF2 (7) and F3CPCH2F (8) (60:35:5).The corresponding reaction of (F3C)2PH with H2N(tBu) mainly yields the compound F3CPCH2F (10).
