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The course of the reactions o f fluorophosphaalkenes F 3 CP = C (F)OR [R = Me (1), Et (2)] with methanol or ethanol strongly depends on the experimental conditions. Thus at 70 °C a mixture of the 2-phosphapropionic acid ester F 3 CP (H )CO 2 R [R = Me (3), Et (4)] and trifluoromethylphosphane H 2 PCF 3  is formed [molar ratio: 3 or 4 /H 2  CF 3  ≈1/1]. If the precursors F 3 CP (H )CO 2 R [R = Me (3), Et) are used as starting materials, the reaction with ROH under the same conditions affords 3 and 4, respectively, (90 to 95% yield) with only traces of H 2 PCF  3 . In the presence o f iPr 2 NH these precursors react with R′OH to give the novel trifluoromethylphosphaalkenes F 3 CP = C (OR )OR [R /R′: Me/Me (6); E t/E t (7); Me/Et (8)]. With Et 2 NH , 3 undergoes an addition/elimination process yielding the interesting push/pull system Et 2 N(F)C = P-CO 2 Me (5). 1 and 2 react with primary amines R′NH 2  (R′=  t Bu, Me) with stereoselective formation of the fairly labile phosphaalkenes F 3 CP = C(OR)NHR′ [R /R′: Me/ t Bu (9), Et/ t Bu(10), Me/Me (11)] with trans-positions for CF 3  and NHR′.The new compounds 3 -11 were characterized by spectroscopic investigations ( 1 H ,  19 F,  31 P,  13 C NMR ; IR, MS) and determination of M +  or typical fragment ions [M +  -OR ] by high resolution mass spectrometry.

zeitschrift für naturforschung b

Reaktive E=C(p–p)π Systeme, XXXIV Addition von Alkoholen oder primären Aminen an Phosphaalkene F 3 CP=C(F)OR. Neue Trifluormethylphosphane und -phosphaalkene/Reactive E = C( p – p ) π-Systems, XXXIV  Addition of Alcohols or Primary Amines to Phosphaalkenes F 3 CP= C(F)OR . Novel Trifluoromethylphosphanes and Phosphaalkenes