SYNTHESIS AND CH-ACIDITY OF N,N-DISUBSTITUTED AMINOTRIPHENYLPHOSPHONIUM SALTS

Article abstract of DOI:10.1007/BF00961243

Several substituted methylaminotriphenylphosphonium salts (APS) of general formula +N(R)CH2R'>X^- have been synthesized.The CH-acidities of some of the prepared APS have been measured by the indicator method in DMSO, with K⁺ counterion and 9-phenylfluorene (pK 18.5) as standard, showing a pK range of 14.7-24.8.The acidification effect of Ph3P⁺N(Ph) (?_CH2^- = 0.70) and Ph3P⁺N(Bu) (?_CH2^- = 0.68) groups has been evaluated.The results obtained suggest that there is an effective charge on the nitrogen atom in the APS studied and an increased multiplicity of the N-P bond.