Interaction of Tris(3-Hydroxymethyl)Phosphine with Cinnamic Acids |
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| Authors: | Dmitry V. Moiseev Brian R. James Aleksey V. Gushchin |
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| Affiliation: | 1. Department of Chemistry , University of British Columbia , Vancouver , British Columbia , Canada;2. Department of Organic Chemistry , Lobachevsky State University of Nizhny Novgorod , Nizhny Novgorod , Russia;3. Department of Chemistry , University of British Columbia , Vancouver , British Columbia , Canada;4. Department of Organic Chemistry , Lobachevsky State University of Nizhny Novgorod , Nizhny Novgorod , Russia |
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| Abstract: | 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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| Keywords: | (3-Hydroxypropyl)phosphine cinnamic acids phosphobetaine diastereomeric ratio |
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