Reaction products of primary β‐hydroxyamines with carbonyl compounds. XIII. Condensation of Primary β‐Mercaptoamines with Carbonyl Compounds
- 1 January 1959
- journal article
- research article
- Published by Wiley in Recueil des Travaux Chimiques des Pays-Bas
- Vol. 78 (4) , 289-314
- https://doi.org/10.1002/recl.19590780410
Abstract
2‐Mercaptoethylamine and 2‐amino‐3‐mercaptobutane have been condensed with various carbonyl compounds. The structure of 14 of these condensation products has been studied by physical methods (molecular refraction, infrared spectrum, ultraviolet spectrum). In all cases, the products formed were thiazolidines and not Schiff bases; in this respect, the 2‐mercaptoamines behave differently from their oxygen isologs.For comparison, the condensations of N‐substituted 2‐mercaptoethylamines with various carbonyl compounds have also been studied (22 examples). The thiazolidine ring causes a depression of the molecular refraction and is characterized by a series of infrared bands in the 1000–1380 cm−1 region. Contrary to the experience with N‐phenylethanolamine, N‐phenyl‐2‐mercaptoethylamine is capable of condensing not only with aldehydes, but also with ketones.Keywords
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