Organophosphorus-Selenium Heteroatom Derivatives from Selenation of Primary/Secondary Amines and Haloalkanes/Dihaloalkanes

Reaction of 2,4-bis(phenyl)-1,3-diselenadiphosphetane-2,4-diselenide (Woollins' reagent) with four equivalents of primary/secondary amines led to a series of ammonium phenylphosphonamido-diselenoates or phenylphosphonamido- diselenoic diamides 1a-n, the latter further reacted in situ with either two equivalents of haloalkanes or an equimolar amount of dihaloalkane, resulting in formation of the corresponding Se-alkylphenyl-Se-alkylphenyl- phosphonamidodiselenoates 2a-n and alkane bis(N-alkyl-P-phenylphosphonamido- diselenoate) derivatives 3a-n in good to excellent yields. All new compounds have been characterized spectroscopically including multinuclear NMR ( H, C, P and Se), IR and mass spectroscopy. Two representative X-ray structures are also described. Woollins' reagent has been applied as a highly efficient building block for the synthesis of organo selenium-phosphorus heteroatom compounds.