Derivatization of Alkyl Halides, Acid Chlorides, and Other Electrophiles with Polymer-Immobilized 8-Amino-2-naphthoxide

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Abstract
Polymer-immobilized 8-amino-2-naphthoxide is used as a labelling reagent for alkyl halides, acid chlorides, and other electrophiles. The derivatives are monitored with UV, oxidative electrochemical, and fluorescence detection. Acid chlorides react fast enough to allow on-line derivatizations. Precolumn and postcolumn derivatizations are possible. Detection limits after derivatization are in the parts-perbillion or sub-parts-per-billion range. Reactions using this solid phase reagent are compared to solution reactions using the sodium salt of 8-amino-2-naphthoxide. In some cases, reactions not possible using the solid phase reagent are carried out with the solution phase reagent. As an application, cis- and trans-1,3-dichloropropene are derivatized in water.