Preparation and 31P nuclear magnetic resonance studies of chiral phosphines

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Abstract
The reaction of Li metal with alkyldiphenylphosphines generates the alkylphenylphosphide anions, which can undergo subsequent reactions with alkyl halides to give chiral phosphines (RR′R″P). The 31P nmr chemical shifts have been measured for these phosphines, and show greater deviations from the values predicted by the first order additivity model than do those of more symmetrical phosphines (i.e., R3P and R2R′P). The shifts for these chiral molecules, and for a wide range of other phosphines, can be accurately predicted using a second order pairwise additivity scheme. The dependence of the observed and calculated chemical shifts upon electronegativity and steric factors is discussed.

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