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Simple enamines derived from acetaldehyde, acetone, and propionaldehyde were generated in situ by iodine oxidation of triethylamine, V,iV-diisopropylmethylamine, and tri-n-propylamine, respectively. The enamines were captured by a variety of cationic substrates including trityl, indolizinium, dithiolium, pyrylium, thiapyrylium, selenapyrylium, and tellurapyrylium cations. The use of a second equivalent of iodine (or excess) oxidized the initial products of enamine capture to various iminium dyes. These dyes were easily hydrolyzed to heterocyclylidene aldehydes and ketones. Cyclic amines such as jV-methylpyrrolidine gave enamines derived from ring oxidation. 2-Cyano-NJV-dimethylethylamine generated a cyano-substituted enamine under the reaction conditions.

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