72217-70-0Relevant articles and documents
SYNTHESE DE PHOSPHONATES β-CARBONYLES I. PAR VOIE CARBANIONIQUE
Aboujaoude, Elie Elia,Collignon, Noel,Savignac, Philippe
, p. 9 - 18 (1984)
Condensation of a lithiated phosphonate carbanion not bearing a stabilizing group with a carbonyl precursor (amide or ester) gives an intermediate oxyanion which decomposes on hydrolysis to yield a β-carbonyl phosphonate.This type of reaction gives access to a large group of phosphonates: β-ketophosphonates, phosphonic aldehydes, phosphonopyruvates etc.The reaction conditions are discussed.
135. Synthesen, chemische Reaktionen und NMR-spectroskopische Untersuchungen substituierter Phosphonopyruvate
Feistauer, Helmut,Neidlein, Richard
, p. 1806 - 1822 (2007/10/02)
Phosphonopyruvates: Syntheses, NMR Investigations, and Reactions.The new 3-(diethoxyphosphoryl)-2-oxopropanoates 5-24 and -propanamides 25-38 with various substituents at C(3) were prepared in moderate-to-good yields (Schemes 2 and 3, Tables 1 and 2).It was shown that they adopt a preferred conformation in which the diethoxyphosphoryl group and the substituent at C(4) are antiperiplanar to each other (see B).The keto-enol tautomerization of phosphonopyruvates with Ph-C(3) (see 20) and MeS-C(3) (see 24 and 33) was examined.In CHCl3, two tautomeric species exist, whereas in dimethylsulfoxide (DMSO), three tautomeric forms are observed.Oxime ethers, an oxime, and a phenylhydrazone of unsubstituted phosphonopyruvates were prepared (see 40-44), and quinoxalin-2(1H)-ones could be obtained from the reaction of pyruvates with 4,5-dimethylbenzene-1,2-diamine (see 45-47).
