Chemistry of Heterocyclic Compounds p. 551 - 557 (1986)
Update date:2022-07-30
Topics:
Ramsh, S. M.
In DMSO-d6 solution 2-hydroxymethylamino-4-thiazolinone, as well as its 5-methyl-congener, exists in the form of E- and Z-conformers relative to the exocyclic nitrogen-carbon bond; for each of these conformers, furthermore, both a transoid and cisoid orientation of the hydrogen and oxygen atoms, relative to the N-CH2 bond, are possible.The transoid form is able to form a chelate derivative with intramolecular hydrogen bond formation.Both acids and bases catalyze transitions among the "open" forms, although chelate formation is only acid-catalyzed.
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