Abstract
The syntheses of alkyl and aryl-substituted tetrakis(amino)phenylphosphonium compounds of type (RNH)4-n (C6H5)nPX, where R = n-C3H7 (1), i-C4H9 (2), n-C4H9 (3), s-C4H9 (4), n-C6H13 (5), c-C6H11 (6), C6H5CH2 (7) and C6H5 (8), and where X = Br, and (C6H5)4B, are described. These compounds have been characterized by elemental analysis, melting point and 1H and 31P NMR spectroscopy. Solubility characteristics in water and organic solvents are given for several derivatives within each series. It has been found that as the number of phenyl substituents on the phosphorus increases, so does the solubility in most solvents investigated. The mild conditions used to synthesize a tetraphenylborate derivative from the corresponding phosphonium bromide indicates the relative ease with which these phosphonium compounds undergo metathesis reactions. Hydrolysis reactions undergone by several partially substituted intermediates, as well as unreacted starting materials have been found to cause lower reaction yields, as evidenced by NMR results. Phosphorus and proton NMR spectra are consistent with a structure for these compounds similar to the regular phosphonium salts, and represented as [(RNH)4-n(C6H5)0P]+X−, where the substituents are tetrahedrally arranged around the phosphorus central atom.