Phosphorylating Power of Red Phosphorus towards Aldehydes in Basic and in Acidic Media

✍ Scribed by Dominique Albouy; Guita Etemad-Moghadam; Max Koenig

• Publisher: John Wiley and Sons
• Year: 1999
• Tongue: English
• Weight: 269 KB
• Volume: 1999
• Category: Article
• ISSN: 1434-193X
• DOI: 10.1002/(sici)1099-0690(199904)1999:4<861::aid-ejoc861>3.0.co;2-j

✦ Synopsis

The reactivity of red phosphorus towards aldehydes was media in the presence of hydriodic acid led to the corresponding phosphonic acids. The (α-hydroxy-investigated under basic and acidic media. It was demonstrated that the real phosphorylating agent involved alkyl)phosphinic acids were readily prepared under sonication from hypophosphorous acid and aldehydes in the in the reaction was phosphane (PH 3 ) in basic media, and hypophosphorous acid (H 3 PO 2 ) in acidic media. A presence of catalytic amounts of hydrochloric acid. The mechanism of the addition reaction of PH 3 to benzaldehyde convenient one-pot synthesis of (α-hydroxyalkyl)phosphinic acids from red phosphorus and aldehydes in basic media was was elucidated and shows the complexity of the reaction as a function of the experimental conditions. realized under sonication. The same reaction under acidic tal phosphorus, due to the large number of oxidized and