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
Open Access
- 1 August 1986
- journal article
- Published by Walter de Gruyter GmbH in Zeitschrift für Naturforschung B
- Vol. 41 (8) , 974-980
- https://doi.org/10.1515/znb-1986-0808
Abstract
Perfluoro-3-phosphapent-2-ene F5C2 P =C (F )CF3 (1) has been prepared for the first time by thermal elimination of trimethyltin fluoride Me3SnF from trim ethylstannyl-bis(pentafluoroethyl)- phosphane Me3SnP(C2F5) 2 at 300 °C/10−3 Torr. 1 is found to be less stable than F3CP = CF2 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, NMe2, NEt2) to the PC double bond affording chiral phosphanes of the type F5C2 P(X)CF(CF3)H [X = OMe (8). Br (9). NMe2 (10). NEt2 (11)]. thus proving a stronger polarity δ+P =δ−C for 1 than for F3CP = CF2. New compounds have been characterized by NMR and MS measurements.Keywords
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