Interaction of 2-methyl-2,5-dioxo-1,2-oxaphospholane with trimethylsilyl cyanide

Article abstract of DOI:10.1007/BF00699999

The reaction of 2-methyl-2,5-dioxo-1,2-oxaphospholane (1) with trimethylsilyl cyanide was found to give, depending on conditions, three organophosphorus compounds: trimethylsilyl methyl(2-cyanocarbonylethyl)phosphinate (2), trimethylsilyl methyl(3-trimethylsiloxy-3,3-dicyanopropyl)phosphinate (3) and trimethylsilyl methyl(3-trimethyl-siloxy-3-cyano-2-propenyl)phosphinate (4).On hydrolysis of 3 under mild conitions, methyl(3-hydroxy-3,3dicarboxypropyl)phosphinic acid (7) was obtained.The latter is readily decarboxylated on heating to give methyl(3-hydroxy-3-carboxy-propyl)phosphinic acid (8).The interaction of 2 and 4 with water or alcohols gives, correspondingly, methyl<2-carboxy(alkoxycarbonyl)ethyl>phosphinic acids (11-13).Methyl(2-oxamoylethyl)phosphinic acid (14) was prepared by successive treatment of propenylphosphinate 4 with HCl gas and water.