Abstract
2-Aminoethanethiol and its derivatives were synthesized in excellent yields from 2-aminoethyl hydrogensulfate and its derivatives with ammonium hydrogensulfide under the mild reaction conditions of 88-66°C and 52 hr.
Although structure C 4 J was expected for the resulting product from the displacement of the sulfate moiety in 2-aminopropyl hydrogensulfate with the hydrogensulfide anion, compound 3J was obtained instead. Thus the aziridine compound was assumed to be the intermediates in the reaction of aminoalkyl hydrogensulfates with ammonium hydrogensulfide as shown in equation ( 2 ). The hydrogensulfide anion was considered to be introduced selectively into the unsubstituted methylene carbon where the steric hindrance to the substitution was minimal.
