857682-82-7Relevant articles and documents
Synthesis of new enantiopure proton-ionizable crown ethers containing a dialkylhydrogenphosphate moiety
Kovacs, Ilona,Huszthy, Peter,Bertha, Ferenc,Sziebert, Denes
, p. 2538 - 2547 (2007/10/03)
Seven new enantiopure proton-ionizable crown ethers containing a dialkylhydrogenphosphate moiety were prepared starting from optically active dialkyl-substituted oligoethylene glycols and phosphorus oxychloride followed by mild hydrolysis of the resulting macrocyclic chlorophosphates. Pentaethylene glycols having primary hydroxyl groups gave good yields of 17-crown-6 type ethers. Pentaethylene glycols with secondary hydroxyl groups rendered about the same amount of 17-crown-6 ethers and open chain dihydrogenphosphates in low yields. Tetraethylene glycols are reluctant to undergo macrocyclization with phosphorus oxychloride, especially the ones which contain secondary hydroxyl groups.