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Perfluoro-3-phosphapent-2-ene F 5 C 2  P =C (F )CF 3  (1) has been prepared for the first time by thermal elimination of trimethyltin fluoride Me 3 SnF from trim ethylstannyl-bis(pentafluoroethyl)- phosphane Me 3 SnP(C 2 F 5 ) 2 at 300 °C/10 −3  Torr. 1 is found to be less stable than F 3 CP = CF 2  in dilute solution at room temperature, forming several 1,3-diphosphabutane dimers. Reactivity studies accomplished till now include (i) the dienophilicity of 1 in [2+4] cycloaddition reactions with butadiene, 2,3-dim ethylbutadiene, cyclopentadiene, 1,3-cyclohexadiene, 2-methylbutadiene, and 2-methylfuran leading by a concerted mechanism to the Diels-Alder-adducts 2-7 in about 80% yield, (ii) the addition of proton acidic compounds HX (X = OMe, Br, NMe 2 , NEt 2 ) to the PC double bond affording chiral phosphanes of the type F 5 C 2  P(X)CF(CF 3 )H [X = OMe (8). Br (9). NMe 2  (10). NEt 2  (11)]. thus proving a stronger polarity  δ+ P = δ− C for 1 than for F 3 CP = CF 2 . New compounds have been characterized by NMR and MS measurements.

zeitschrift für naturforschung b

Reaktive E =C (p—p)π-Systeme, X Darstellung und Reaktivität von Perfluor-3-phosphapent-2-en / Reactive E = C (p-p)π-Systems, X Preparation and Reactivity of Perfluoro-3-phosphapent-2-ene