Kinetic and thermodynamic control in the formation of monoacetals from aldehydes and D-glucitol
- 1 January 1968
- journal article
- research article
- Published by Royal Society of Chemistry (RSC) in Journal of the Chemical Society B: Physical Organic
- p. 827-830
- https://doi.org/10.1039/j29680000827
Abstract
The formation under kinetic control of a 2,3-O-monoacetal in the reaction of an aldehyde with D-glucitol in acid solution, first shown to occur with n-butyraldehyde, has now been observed with both benzaldehyde and acetaldehyde. Hydrolysis of the 2,3-O-ethylidene acetal in aqueous acid gives substantial fission of the acetal ring followed by recombination to the 2,4-acetal. The 2,3-O-benzylidene acetal appears to undergo ring migration to the 2,4-acetal in anhydrous media.Keywords
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