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Mechanism of Base-catalysed Hydrogen-Deuterium Exchange in Thiazolium Ion: Evidence for the Involvement of a Tetrahedral Intermediate

DOI: 10.1039/P29810001538

Source and publish data:

Journal of the Chemical Society. Perkin transactions II p. 1538 - 1543 (1981)

Update date:2022-09-26

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Authors:

Karimian, KhashayarKarimian, Khashayar

Mohtarami, FatemehMohtarami, Fatemeh

Askari, MassoudAskari, Massoud

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Article abstract of DOI:10.1039/P29810001538

The mechanism of base-catalysed hydrogen-deuterium exchange of 2-H in the thiazolium ion has been examined by 1H n.m.r. spectroscopy, using small and sterically hindered nucleophiles.Rapid H-D exchange is observed in <(2)H6>Me2SO in the cases of 3,4,5-trimethyl- (1), 3-methyl-4,5-diphenyl- (2), 3,5-dimethyl-4-phenyl- (3), and 3,4-dimethyl-5-phenyl-thiazolium iodide (4), when small nucleophiles (KOD-D2O or KOCD3-DOCD3; 0.016M; 25 deg C) are employed.Utilization of a hindered nucleophile however results in a slow exhange of 2-H in (1), (3), and (4), concomitant with H-D exchange of the 4- and 5-methyl exchange of 2-H is detected in the case of (2) with the hindered nucleophile.These observations are ascribed to the formation of a tetrahedral intermediate as a prerequisite of the exchange reaction.

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Product name:3,5-dimethyl-4-phenylthiazolium iodide

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