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Kinetics and mechanism of the acid-catalyzed hydration of dihydro-1,4-dioxin (1989)

Kresge, A. J. ; Yin, Y.

Chichester : Wiley-Blackwell

Journal of Physical Organic Chemistry 2 (1989), S. 43-50

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ISSN: 0894-3230

Keywords: Organic Chemistry ; Physical Chemistry

Source: Wiley InterScience Backfile Collection 1832-2000

Topics: Chemistry and Pharmacology , Physics

Notes: The cyclic vinyl ether dihydro-1,4-dioxin is converted to its cyclic hemiacetal hydration product, 2-hydroxy-1,4-dioxane, in aqueous solution by an acid-catalyzed reaction for which kH+ = 1·80 × 10-5 M-1 S-1 at 25°C. This reactivity and the solvent isotope effect kH+/kD+ = 2·2 show that the reaction occurs by rate-determining proton transfer from catalyst to substrate and not by a pre-equilibrium mechanism as recently proposed.2

Additional Material: 1 Ill.

Type of Medium: Electronic Resource

URL: http://dx.doi.org/10.1002/poc.610020106

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