Utilization of the Sterically Hindered Base, 4-Hydroxy-2,2,6,6-tetramethylpiperidine, as a Hydrogen Halide Acceptor

Abstract

<jats:p>The synthetic utility of the sterically hindered base, 4-hydroxy-2,2,6,6-tetramethylpiperidine (1) as a hydrogen halide acceptor was studied.</jats:p><jats:p><jats:inline-formula><jats:alternatives><jats:inline-graphic xmlns:xlink="http://www.w3.org/1999/xlink" xlink:href="graphic/Untitled-2.jpg" /></jats:alternatives></jats:inline-formula></jats:p><jats:p> It was shown that base 1 can be effectively used in the quaternization reaction of primary aliphatic and aromatic amines to give the corresponding trimethylammonium iodides 2 in 88-98% yield. Base 1 was used also as the dehydrobrominating agent of alkyl and cycloalkyl bromides to give the corresponding unsaturated compounds in 82-95% yield.</jats:p>