Abstract
Phosphonium zwitterions of the known type R3P+CH(Ar)CH2CO2 − (II) are obtained as a racemic mixture in moderate yield via a 1:1 reaction of cinnamic acids (Ar = phenyl, or substituted phenyl) with [HO(CH2)3]3P in acetone at room temperature under Ar. The products are characterized by elemental analysis, 31P{1H}-, 1H-, and 13C{1H}-NMR spectroscopies, and mass spectrometry, although they contain a minor coproduct formed via neutralization of the positive and negative charges of II with the respective acid and phosphine reactants (see Experimental Section). In CD3OD, the monodeuterated salts R3P+CH(Ar)CH(D)CO2 − are formed as a mixture of diastereomers with d.r. values of ∼2 to 8, depending on substituent groups present in the organic acid; in these studies, 2-HO-cinnamic acid is the most reactive, and β-methylcinnamic acid is the least reactive.
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