ChemInform Abstract: REACTIONS OF OXAZAPHOSPHOLANES WITH CARBOXYLIC ACIDS

Abstract

Das 2‐Diethylamino‐ 1,3,2‐Oxazaphospholan (I) reagiert mit Essigsäure (II) zur Zwischenstufe (III), die ohne Isolierung direkt einer Todd‐Atherton‐Reaktion unterworfen wird, wobei man das 1,3,2‐Oxazaphospholan (IV) erhält.

Amides of Trivalent Phosphorus Acids as Phosphorylating Reagents for Proton-Donating Nucleophiles

“…Attention is focused on the design of phosphorus-containing heterocycles. It was shown that phosphorus-containing reagents whose molecules contain two or three amido groups readily phosphorylate equimolar amounts of 1,2- and-1,3-amino alcohols including derivatives of 1,2-ethanolamine, ,,,,− 1,3-propanolamine, ,− and prolinol , to afford 1,3,2-oxazaphospholanes (Scheme ) and -phosphorinanes. 1-Desoxy-1-aminosaccharides and 1- N -hydroxyethyl-3-iminopyrazoline are phosphorylated in a similar way.…”

“…Subsequently, this reaction has been further developed regarding its use for synthetic purposes. ,,,, It became clear that excess acid is needed to neutralize the secondary amine being evolved, because the amine can attack the carbonyl group in acyl phosphite as a hard nucleophile. In fact, the use of equimolar amounts of the reactants gives a totally different result (Scheme ). , …”

“…The latter reaction has proved to be highly fruitful and found application in the solution of various chemical problems. It can be carried out for phosphorus mono-, ,, di-, , triamides 497,643,648 and phosphonous amides. , According to the desire of the researcher, di- and triamides can be dealkylated either partially 648,649 or completely . Note that the greater part of works were devoted to acidolysis of cyclic ATPA.…”

“…It can be carried out for phosphorus mono-, 216,646,647 di-, 648,649 triamides 497,643,648 and phosphonous amides. 514,644 According to the desire of the researcher, di-and triamides can be dealkylated either partially 648,649 or completely. 497 Note that the greater part of works were devoted to acidolysis of cyclic ATPA.…”