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Trimethylsilyl phosphines Ph(R)PSiMe 3  (R = Me, Et, Pr, Bu, iBu, and C 5 H 11 ) react with acrylic esters CH 2  = C(R′)CO 2 Me(R′ = H, Me) to give the O-silylated phosphinoketenacetals Ph(R)PCH 2 C(R′)=C(OSiMe 3 )OMe 1-6, 15 and 16. By contrast, the reactions of the sterically demanding silyl phosphines R 2 PSiMe 3  (R = iPr, tBu) with CH 2 = CHCO 2 R′ (R′ = Me, Et) result in the formation of mixtures of the corresponding phosphinoketenacetals 7-10 and the 1,2-addition products R 2 PCH 2 CH(SiMe 3 )CO 2 R′ 11-14. The ratio of the two isomers depends on the solvent and on the reaction temperature. β-Substituted acrylic acid esters such as methyl trans-crotonate or methyl trans-cinnamate react only very slowly (yielding a mixture of compounds) or do not react at all. NMR spectra and NOE measurements reveal that only the Z-isomer of the O-silylated phosphinoketenacetals is formed. On the basis of these results a plausible reaction mechanism is proposed. The phosphinoketenacetals react with H 2 O to afford the phosphinoesters R(R′)PCH 2 CH 2 CO 2 R″ 17-22, and with D 2 O to give the deuterated species R(R′)PCH 2 CHDCO 2 Me 23 and 24.

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O-Silylierte Phosphinoketenacetale RR′PCH 2 CH=C(OSiMe 3 )OR″. Darstellung und Hydrolyse zu Phosphinoestern / O -Silylated Phosphinoketenacetals RR′PCH 2 CH = C(O SiMe 3 )OR″. Preparation and Hydrolysis to Phosphinoesters