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Described here is the nucleophilic substitution of a hydroxyl group, in cinnamyl alcohol, by fluorine, and analysis of the product using 19-F NMR spectroscopy. This experiment brings important innovations to the teaching of experimental organic chemistry at the undergraduate level. The fluorination of cinnamyl alcohol requires only a mild fluorinating agent and so it provides the student with a direct contact with organofluorine, chemistry. The allylic nucleophilic substitution typified by our experiment will enhance the instruction of nucleophilic substitution in the laboratory, traditionally limited to SN1 or SN2 substitutions. Because the ratio of SN2 to SN2' derived products cannot be determined directly using 1-H NMR spectroscopy but it can be measured easily using 19-F NMR spectroscopy. The experiment gives the student a firsthand experience of the usefulness of NMR spectra of different nuclei.

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An Efficient Synthesis of (Z)-γ-Fluoroallylphosphonates Using a Base-Promoted Deconjugation of (E)-γ-Fluorovinylphosphonates, and Its Utility as Fluoroolefin-Containing Building Block.-A facile threestep synthesis of γ-fluoroallylphosphonates (V) via a modified Pudovik reaction of α,β-unsaturated aldehydes with diethyl phosphite, DAST deoxyfluorination of the resulting hydroxyallylphosphonates (III), and finally, base-promoted double bond migration is described. Moreover, scope and limitation of this approach as well as some reactions of the title γ-fluoroallylphosphonates are studied. -(HAMMOND, GERALD B.; DEMENDONCA, DANIEL J.; J.