2-Ethoxyvinyl)triphenylphosphonium-bromid (5) lafit sich rnit Natriumamid in das korrespondierende Phosphaallenylid 6 uberfiihren, das Ethanol zum Ylid 7 addiert. 7 wird auch aus 5 rnit Natriumethylat erhalten. Die Wittig-Reaktion von 7 rnit Aldehyden 2 verlauft rnit hoher (Z)-Stereoselektivitat. Die entstehenden (Z)-a,O-ungesattigten Acetale 8 lassen sich unter Einhaltung definierter Bedingungen mit p-Toluolsulfonsaure oder durch feuchtes Kieselgel zu den (Z)-a,pungesattigten Aldehyden 9 spalten.(2-Ethoxyvinyl)triphenylphosphonium bromide (5) is converted with sodium amide into the corresponding phosphaallenylide 6 which adds ethanol forming the ylide 7. 7 is also obtained by the reaction of 5 with sodium ethanolate. The Wittig reaction of 7 with aldehydes 2 proceeds with high (Z)-stereoselectivity to give (Z)-a, O-unsaturated acetals 8 which are cleaved under well defined conditions with p-toluenesulfonic acid or with wet silica gel to (Z)-a,p-unsaturated aldehydes 9.
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