84261-67-6Relevant academic research and scientific papers
Enamines from Iodine Oxidation of Trialkylamines. 1. Electrophilic Capture by Cationic Heterocyclic Rings
Wadsworth, Donald H.,Detty, Michael R.,Murray, Bruce J.,Weidner, Charles H.,Haley, Neil F.
, p. 2676 - 2681 (2007/10/02)
Simple enamines derived from acetaldehyde, acetone, and propionaldehyde were generated in situ by iodine oxidation of triethylamine, N,N-diisopropylmethylamine, and tri-n-propylamine, respectively.The enamines were captured by a variety of cationic substrates including trityl, indolizinium, dithiolium, pyrylium, thiapyrylium, selenapyrylium, and tellapyrylium 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 N-methylpyrrolidine gave enamines derived from ring oxidation. 2-Cyano-N,N-dimethylethylamine generated a cyano-substituted enamine under the reaction conditions.
