Enamines from iodine oxidation of trialkylamines. 1. Electrophilic capture by cationic heterocyclic rings

DH Wadsworth, MR Detty, BJ Murray…

Index: Wadsworth, Donald H.; Detty, Michael R.; Murray, Bruce J.; Weidner, Charles H.; Haley, Neil F. Journal of Organic Chemistry, 1984 , vol. 49, # 15 p. 2676 - 2681

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Citation Number: 22

Abstract

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, indoliziium, dithiolium, pyrylium, thiapyrylium, selenapyrylium, and tellurapyrylium cations. The use of a second equivalent of iodine (or excess) oxidized the ...