1969
DOI: 10.1039/j29690001031
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Specific acid catalysis in acetal hydrolysis

Abstract: The hydrolyses of benzaldehyde diethyl acetal. benzophenone diethyl ketal, and methyl 2,5-anhydro-a-~-arabinofuranoside are shown to be specific-acid catalysed.ACETAL hydrolysis 1 is a classic example of a specific-acid catalysed reaction. Brprnsted and Wynne-Jones,2 using formic acid-formate buffers (concentration of formic acid 0.0037-0.1194~) were unable to detect any buffer catalysis in the hydrolysis of diethyl acetal. Brprnsted and Grove3 showed that phenol (up to 0.20M) did not increase the rate of hydr… Show more

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Cited by 3 publications
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“…Finally, we note that the extent of C-0 bond cleavage 66 in the transition state also is correlated with solvent deuterium isotope effects: the less covalent bond cleavage, the smaller the solvent isotope effect (Table I I I ) . Taken together, these three lines of evidence provide a rather persuasive case for the transition state structures as noted above.…”
Section: E H Cordes and H G Bullmentioning
confidence: 85%
“…Finally, we note that the extent of C-0 bond cleavage 66 in the transition state also is correlated with solvent deuterium isotope effects: the less covalent bond cleavage, the smaller the solvent isotope effect (Table I I I ) . Taken together, these three lines of evidence provide a rather persuasive case for the transition state structures as noted above.…”
Section: E H Cordes and H G Bullmentioning
confidence: 85%
“…Besides hydrogenation of aldehydes to afford alcohols, hydrogenolysis of ketals/acetals is another pathway to obtain alcohols (or the corresponding ethers) over acidic transition metal catalysts. Inspired by the facts including hydrogenolysis of acetals to yield alcohols (or ethers) and the successful hyroformylation–acetalization over the bifunctional catalyst reported by us, , we first proposed a three-step tandem reaction to produce alcohols (derivatives) from olefins via hydroformylation of olefins, acetalization of aldehydes, and hydrogenolysis of acetals (Scheme ). In this tandem process, the easily accomplished acetalization served as a transition step to get through the pathway from aldehydes to alcohols instead of direct hydrogenation.…”
Section: Introductionmentioning
confidence: 99%