Wasserloesliche Phosphane. II. Ein neuer Syntheseweg fuer wasserloesliche sekundaere und tertiaere Phosphane mit sulfonierten aromatischen Resten - Kristallstruktur von P(p-C6H4-SO3K)3*KCl*0.5H2O

Article abstract of DOI:10.1016/0022-328X(94)84012-1

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 HP2 (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 1H, 13C<1H> and 31P<1H> 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)^o) and P-C bond lengths (1.843(4) Angstroem) being almost identical to those in Ph3P.Key words: Phosphine; Catalysis; Nuclear magnetic resonance; Water soluble phosphine; Phase transfer; Hydroformylation