Journal
ORGANIC LETTERS
Volume 3, Issue 23, Pages 3655-3658Publisher
AMER CHEMICAL SOC
DOI: 10.1021/ol010175t
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[GRAPHICS] It is possible to correlate the distribution of stereochemical products produced during a Hantzsch thiazole synthesis according to the Hammett free-energy equation. This analysis confirms the presumed control of the rate of epimerization during thiazole formation due to stabilization of a cationic transition state intermediate during dehydration of the thiazoline ring system. In the chemical system under study, the stereochemical outcome of the reaction also appears to occur according to a kinetically controlled protonation of a thiazoline tautomer.
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