Journal of the Chemical Society. Perkin transactions II p. 825 - 828 (1980)
Update date:2022-08-03
Topics:
Senogles, Ernest
Thomas, Roderick A.
The kinetics and mechanism of the acid-catalysed hydrolysis of N-vinylpyrrolidin-2-one (1) has been studied using n.m.r. spectroscopy and spectrophotometry.At temperatures near 0 deg C N-(1-hydroxyethyl)pyrrolidine-2-one (3) is the main product.At higher temperatures this decomposes into acetaldehyde and pyrrolidin-2-one (4) and the latter reacts with an excess of N-vinylpyrrolidine-2-one to give 1,1-bis-(N-2-oxopyrrolidinyl)ethane (5).The rate determining step of the hydrolysis reaction has been established as proton transfer to N-vinylpyrrolidin-2-one and the reaction conforms to a general acid catalysis mechanism.A Broensted exponent value of 0.68 +/- 0.03 was obtained with a series of carboxylic acids.
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