69054-07-5Relevant academic research and scientific papers
SYNTHESIS AND CHEMICAL PROPERTIES OF SUBSTITUTED 2-HYDROXY-2-PHOSPHONYLETHANALS AND 1,2-DIHYDROXY-1,2-BISPHOSPHONYLETHANES
Mikroyannidis, John A.,Tsolis, Alexandros K.,Gourghiotis, Simitrios J.
, p. 279 - 290 (2007/10/02)
The syntheses of 2-hydroxy-2-(dialkoxyphosphonyl)ethanals 1a-1h, and of 1.2-dihydroxy-1,2-bis(dialkoxyphosphonyl)ethanes 2a-2h by reactions of glyoxal with phosphorus acid diesters in acidic medium are reported.The base catalyzed isomerization of 2-hydroxy-2-(dialkoxyphosphonyl)ethanals 1 to formylmethylphosphates 3 was demonstrated by 31P NMR spectroscopy.The stability of 1,2-dihydroxy-1,2-bis-(dialkoxyphosphonyl)ethanes 2 towards bases was demonstrated and interpreted on the basis of their structural features.The reactions of glyoxal with O-(n-butyl)phenylphosphonite, diethyl- and diphenylphosphine oxide and the indentification of their products are reported as well as the synthesis of 1,2-dihydroxy-1,2-bis(dihydroxyphosphonyl)ethane 2m by acid-catalysed hydrolysis of 1,2-dihydroxy-1,2-bis(dialkoxyphosphonyl)ethanes and by hydrogenation of 1,2-dihydroxy-1,2-bis(dibenzyloxyphosphonyl)ethane 2f.The rate constant of the hydrogenation of 2f and the pKa values of the 1,2-dihydroxy-1,2-bis(dihydroxyphosphonyl)ethane 2m are also reported.
