Ammonium Phenylphosphonamidodiselenoates and Phenylphosphonamidodi-selenoic Diamides from the Selenation of Primary and Secondary Amines

Abstract

By reacting two equivalents of primary or secondary amines with 2,4-bis(phenyl)-1,3-diselenadiphosphetane-2,4-diselenide (Woollins' reagent) at room temperature a series of new ammonium phenylphosphonamidodiselenoates 1-7 have been obtained in good to excellent yields (70-99 %). The first metal complex of phenylphosphonamidodiselenoate, the complex of Cd2L4 (L = [Se2PPh(NCH(CH3)(2)](-)) (8) has been prepared from the reaction of diisopropylamine N-isopropyl-P-phenylphosphonamidodiselenoate with Cd(CH3COO)(2) in dichloromethane. Upon heating to 130 degrees C the ammonium phenylphosphonamidodiselenoates lose hydrogen selenide leading to the corresponding phenylphosphonamidodiselenoic diamides 9-11 in almost quantitative yields. The same products 9-11 can also be prepared directly from the reaction of primary amines with Woollins' reagent in refluxing toluene. Three representative X-ray structures are described.