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Original Articles

α-SUBSTITUIERTE PHOSPHONATE 671. ZUR REAKTION VON SALICYLALDEHYD MIT TRIETHYLPHOSPHIT. EINE NEUE C → O-PHOSPHORYLGRUPPENUMLAGERUNG

, , , &
Pages 121-128 | Received 03 Aug 1993, Accepted 24 Aug 1993, Published online: 23 Sep 2006
 

Abstract

Bei Versuchen zur Synthese des 2-Hydroxy-phenylmethan-bisphosphonates 6 aus Salicylaldehyd und Triethylphosphit erhielten wir in Abhängigkeit von der Reaktionstemperatur jeweils ein komplexes Gemisch unterschiedlicher Produkte, von denen sich einige in reiner Form isolieren und strukturell absichern ließen. 6 wurde nicht erhalten, statt dessen der Phosphat-Phosphonat-Ester 14. Die auch auf unabhängigem Wege bewiesene Umwandlung von 6 in 14 entspricht einer neuen C → O-Phosphoryl-gruppenumlagerung.

Attempting to prepare the 2-hydroxy-phenylmethane-bisphosphonate 6 from salicyaldehyd and triethylphosphite depending on the temperature of the reaction in each case a complex mixture of different products were formed, some of them we could isolate in pure form and prove the structure. Instead of 6 we isolated the phosphate-phosphonate-ester 14. The conversion of the preformed 6 to 14, which we could prove independently, presents a new C → O-phosphoryl group rearrangement.

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