Development of an atom economical method for phosphenium cation synthesis
LE3 .A278 2013
Bachelor of Science
N,C-bound dibromophosphine compounds were produced through the reaction of an aryl Grignard reagent with PBr3 (Aryl substituent = Tripp = triisopropylphenyl / TerMes = 2,6-bis(2,4,6-trimethylphenyl)phenyl) and was characterized through 31P NMR spectroscopy. Through a reaction with diisopropylamine, an N,C-bound monobromophosphine was formed which was also characterized by 31P NMR spectroscopy. An attempt was made to produce phosphenium cations from these synthesized monobromophosphine compounds through halide abstraction by Lewis acidic Al2Cl6 to remove the remaining bromide anion, leaving a phosphorus(III) cationic centre still containing an aryl and amido substituents and a AlCl3Br- counter ion. The synthetic steps, including production of an aryl Grignard reagent, organolithium reagent, C-P bond formation, and amination, were successful until the halide abstraction in which a 31P NMR peak was not observed at the expected chemical shift range of approximately 500 ppm. This multiple unexpected NMR peaks were indicative of moisture contamination of the reaction mixture.
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