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Ammonium Phenylphosphonamidodiselenoates and Phenylphosphonamidodi‐selenoic Diamides from the Selenation of Primary and Secondary Amines
Author(s) -
Hua Guoxiong,
Randall Rebecca A. M.,
Slawin Alexandra M. Z.,
Woollins J. Derek
Publication year - 2011
Publication title -
zeitschrift für anorganische und allgemeine chemie
Language(s) - English
Resource type - Journals
SCImago Journal Rank - 0.354
H-Index - 66
eISSN - 1521-3749
pISSN - 0044-2313
DOI - 10.1002/zaac.201100257
Subject(s) - chemistry , reagent , dichloromethane , primary (astronomy) , diselenide , selenide , ammonium , medicinal chemistry , toluene , isopropyl , organic chemistry , selenium , solvent , physics , astronomy
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 Cd 2 L 4 (L = [Se 2 PPh(NCH(CH 3 ) 2 ] – ) ( 8 ) has been prepared from the reaction of diisopropylamine N ‐isopropyl‐ P ‐phenylphosphonamidodiselenoate with Cd(CH 3 COO) 2 in dichloromethane. Upon heating to 130 °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.