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The vapour phase pyrolysis of the stannylphosphane Me 3 SnP(CF3)C 2 F 5  (5) at 330 °C leads to 1,2-elimination of Me 3 SnF yielding a mixture of the two isomeric perfluorophosphaalkenes F 3 CP=C(F)CF 3  (3) and F 5 C 2 P=CF 2  (4) in a 3:1 molar ratio. 3 is more labile than 4 and proves to be similar to the perfluoro-3-phosphapent-2-ene F 5 C 2 P=C(F)CF 3  (2) with respect to NMR data and chemical properties. On the other hand 4 resembles the perfluoro-2-phosphapropene F 3 CP=CF 2  (1). These results have been deduced from the following reactivity studies: (i) The rate of dimerization being higher for 3 than for 4. (ii) Reaction of the mixture with diethylamine yielding the aminophosphane derivative F 3 CP(NEt 2 )CF(H)CF 3  (13) as a product of 3 and the C-aminophosphaalkene F 5 C 2 P=C(F)NEt 2  (14) as the derivative of 4. (iii) Reaction of the mixture with methanol giving the methoxyphosphane F 3 CP(OMe)CF(H)CF 3  (15) from 3 and the secondary phosphane F 5 C 2 P(H)CF 2 OMe (16) from 4 as precursors. 3 and 4 prove to be effective dienophiles in reactions with 2,3-dimethyl-1,3-butadiene and 1,3-cyclohexadiene, respectively, producing the corresponding Diels-Alder adducts 9 to 12. For these preparations 5 can be used as an equivalent of 3 in a one-pot procedure at 70 °C. On the other hand the phosphane HP(CF 3 )C 2 F 5  (8) is suited as precursor for 3 in preparing HX addition products.

zeitschrift für naturforschung b

Reaktive E=C(p – p)π-Systeme, XX [1] / Reactive E=C(p–p)π-Systems, XX [1]: Synthese und Reaktivität der konstitutionsisomeren Perfluorphosphaalkene F 3 CP=C(F)CF 3  und F 5 C 2 P=CF 2  / Synthesis and Reactivity of the Isomeric Perfluorophosphaalkenes F 3 CP=C(F)CF 3  and F 5 C 2 P=CF 2