Schiff's bases as intermediates in the hydrolytic decomposition of 2-alkyl-3-methyl-1,3-oxazolidines in aqueous acid
- 1 January 1983
- journal article
- research article
- Published by Royal Society of Chemistry (RSC) in Journal of the Chemical Society, Perkin Transactions 2
- No. 8,p. 1223-1226
- https://doi.org/10.1039/p29830001223
Abstract
The kinetics for the hydrolysis of 2-alkyl-3-methyl-1,3-oxazolidines have been examined spectrophotometrically in acidic solutions. The decomposition of the substrates to 2-methylaminoethanol and the corresponding aldehydes have been shown to proceed via stable intermediates which are kinetically and u.v.-spectroscopically very similar to the acyclic cationic Schiff's base derived from isobutyraldehyde and 2-methoxyethylmethylamine. The mechanisms for the formation and breakdown of the Schiff's base intermediate are discussed on the basis of pH–rate profiles, activation parameters, salt effects, and solvent deuterium isotope effects.Keywords
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