WATER-SOLUBLE PHOSPHANES .2. NEW METHOD FOR SYNTHESIS OF WATER-SOLUBLE SECONDARY AND TERTIARY PHOSPHANES WITH SULFONATED AROMATIC RESIDUES - CRYSTAL-STRUCTURE OF P(PARA-C6H4-SO3K)3.KCL.0.5H2O

Water soluble tertiary phosphanes 2, 7, 10-17 with sulfonated aromatic substituents P-C6H4-SO3K and 2,4-C6H3(SO3K)2 can be obtained in good yields by nucleophilic aromatic substitution of fluorine in p-F-C6H4-SO3K (1) or F-C6H3-2,4-(SO3K)2 (5) with PH3 or Primary and secondary phosphanes in the superbasic medium dimethyl sulfoxide (DMSO)/KOH(solid). The first water-soluble secondary phosphane HP[C6H3-2,4-(SO3K)2]2 (6) having sulfonated aromatic substituents can be obtained if 5 is reacted under similar conditions with PH3. Highly sulfonated phosphanes (7-9) with remarkable solubilities in water are formed upon reaction of 6 with F-C6H5, (n)BuBr or C6H5-CH2-Br, respectively, in the superbasic medium. The resulting compounds have been identified by their H-1, C-13{H-1} and P-31{H-1} NMR spectra. X-Ray structural analysis Of P(P-C6H4-SO3K)3 . KCl . 0.5H2O shows C3 symmetry for the trianion of 2 with the P-C-P bond angles (103.5(2)-degrees) and P-C bond lengths (1.843(4) angstrom) being almost identical to those in Ph3P.